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Fluorinated Surfactants : industrial synthetic routes

PFOS : perfluoro-octanesulfonic acid PFOA : perfluoro-octanoic acid HFPO-DA : hexafluoropropylene oxide dimer acid Order Now : (paperback) → https://amz.run/5A69 The “Handbook for Chemical Engineers and Entrepreneurs” is part of Chemiprobe project that aims to visualize the chemical value chain and turn chemical engineers into «chempreneurs» pursuing clear opportunities in commodities and fine chemicals. https://www.chemiprobe.com

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Download to read offline
This handbook is invaluable
to unfold the chemical value
chain in case you were a
process designing chemical
engineer, or an entrepreneur
pursuing an opportunity in
the chemical market.
Hint : chemical price
analysis requires
comprehensive
understanding of the
production process,
precursors and products
along the value chain.
The “Handbook for Chemical Engineers and
Entrepreneurs” is part of Chemiprobe project that aims to
visualize the chemical value chain and turn chemical
engineers into «chempreneurs» pursuing clear
opportunities in commodities and fine chemicals.
Order Now : (paperback) → https://amz.run/5A69
https://www.chemiprobe.com
How To Use This Handbook
This handbook does not requires you to start at the top of
the table of contents and linearly work your way through
to the end; although that may be essential to gain
perspective about commodity chemicals including
petrochemicals, inorganics, and bio-refinery chemicals.
The chemical finder can be used to find a specific
chemical, very much like most indexes in which chemicals
are listed in alphabetical order. On the other hand, the
table of contents lists chemicals with reference to position
along the chemical value chain that is further illustrated
using diagrams. For each chemical in this handbook, you
will find :
- common name, synonyms, chemical structure
- phrases describing appearance and odor (25 °C , atm)
- relative density, melting point, and boiling point
- safety diamond (NFPA 704 for additional notes)
- applications, submarkets, color code
- industrial synthetic route (reaction)
- process description and simplified flow diagrams
commodity chemical production
direct use (no reaction)
formulation and mixing use (no reaction)
fuel, energy , flue gas treatment , heat transfer fluids
plastics and resins
synthetic rubber
polymeric foam , ploymeric fiber
fine chemical synthesis (general)
fine chemical synthesis (pharmaceuticals)
fine chemical synthesis (agrochemicals-pesticides)
production (agrochemicals-fertilizer)
Process Description
Production is based on electrochemical fluorination of alkyl
sulfonyl fluoride -using anhydrous hydrogen fluoride as
electrolyte- forming perfluoro-alkyl sulfonyl fluoride that is
hydrolyzed in another reactor forming the analogous
perfluoro-alkyl sulfonic acid.
The raw material is n-paraffin or refinery fraction of n-
paraffins that is sulfo-chlorinated using sulfur dioxide and
chlorine forming alkyl sulfonyl chloride, which is further
reacted with anhydrous hydrogen fluoride forming alkyl
sulfonyl fluoride. The sulfo-chlorination reaction is carried
out preferably inside bubble-column reactor. Optimum
temperature range (40 ºC – 50 ºC) and pressure in the
atmospheric range regarding the continuous venting to the
phase separator.
After leaving the sulfo-chlorination reactor, the effluent is
cooled and sent to phase separator, the vapor phase
containing hydrogen chloride, and traces of sulfur dioxide
is sent to scrubber in which dilute hydrochloric acid wash
captures hydrogen chloride byproduct and recover sulfur
dioxide as sulfuric acid.
perfluoro-octanesulfonic acid
Appearance 25 °C , atm
white corrosive solid
faint irritating odor
Relative Density 1.84 * (H2O = 1)
Melting Point - 090
Boiling Point - 260
Flash Point - 0--
Synonyms PFOS
foaming agent fire fighting foam
impregnating agent textiles
mist suppresant metal plating electrolysis
emulsifier polytetrafluoroethylene
perfluoro-elastomers synthetic rubber
The liquid phase is sent to the fluorination reactor in which
liquid effluent is reacted with liquid anhydrous hydrogen
fluoride. Optimum temperature range (15 ºC – 20 ºC).
The produced alkyl sulfonyl fluoride is sent to the
electrolytic cell. The oxidation reaction or loss of electrons
takes place on the anode producing perfluo-alkyl sulfonyl
fluoride, and the reduction reaction or gain of electrons takes
place on the cathode producing hydrogen byproduct.
After leaving the electrolytic cell, the effluent is further
hydrolyzed and separated using distillation, not difficult
because of the comparatively distinctive boiling points of
perfluoro-alkyl sulfonic acids. Practically, the yield
decreases with increasing chain length.
Fluorinated Surfactants : industrial synthetic routes
Process Description
Production is based on electrochemical fluorination of alkyl
acyl fluoride -using anhydrous hydrogen fluoride as
electrolyte- forming perfluoro-alkyl acyl fluoride that is
hydrolyzed in another reactor forming the analogous
perfluoro-alkyl carboxylic acid.
The raw material is n-carboxylic acid, that is chlorinated using
thionyl dichloride forming alkyl acyl chloride and is further
reacted with anhydrous hydrogen fluoride forming alkyl acyl
fluoride. The chlorination reaction is carried out inside
agitator-stirred tank or column reactor, in which thionyl
chloride is introduced in portions to maintain temperature
control. Optimum temperature range (40 ºC – 90 ºC) and
pressure in the atmospheric range. During the reaction,
sulfur dioxide is vented and sent to treatment unit.
After leaving the reactor, the liquid effluent is separated in
distillation column, not difficult because of the
comparatively distinctive boiling points of carboxylic acid
and the analogous acyl chloride.
perfluoro-octanoic acid
Appearance 25 °C , atm
white corrosive solid
pungent irritating odor
Relative Density 1.80 * (H2O = 1)
Melting Point - 054
Boiling Point - 192
Flash Point - 0--
Synonyms PFOA
foaming agent fire fighting foam
impregnating agent textiles
mist suppresant metal plating electrolysis
emulsifier polytetrafluoroethylene
perfluoro-elastomers synthetic rubber

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Fluorinated Surfactants : industrial synthetic routes

  • 1. This handbook is invaluable to unfold the chemical value chain in case you were a process designing chemical engineer, or an entrepreneur pursuing an opportunity in the chemical market. Hint : chemical price analysis requires comprehensive understanding of the production process, precursors and products along the value chain. The “Handbook for Chemical Engineers and Entrepreneurs” is part of Chemiprobe project that aims to visualize the chemical value chain and turn chemical engineers into «chempreneurs» pursuing clear opportunities in commodities and fine chemicals. Order Now : (paperback) → https://amz.run/5A69 https://www.chemiprobe.com
  • 2. How To Use This Handbook This handbook does not requires you to start at the top of the table of contents and linearly work your way through to the end; although that may be essential to gain perspective about commodity chemicals including petrochemicals, inorganics, and bio-refinery chemicals. The chemical finder can be used to find a specific chemical, very much like most indexes in which chemicals are listed in alphabetical order. On the other hand, the table of contents lists chemicals with reference to position along the chemical value chain that is further illustrated using diagrams. For each chemical in this handbook, you will find : - common name, synonyms, chemical structure - phrases describing appearance and odor (25 °C , atm) - relative density, melting point, and boiling point - safety diamond (NFPA 704 for additional notes) - applications, submarkets, color code - industrial synthetic route (reaction) - process description and simplified flow diagrams commodity chemical production direct use (no reaction) formulation and mixing use (no reaction) fuel, energy , flue gas treatment , heat transfer fluids plastics and resins synthetic rubber polymeric foam , ploymeric fiber fine chemical synthesis (general) fine chemical synthesis (pharmaceuticals) fine chemical synthesis (agrochemicals-pesticides) production (agrochemicals-fertilizer)
  • 3. Process Description Production is based on electrochemical fluorination of alkyl sulfonyl fluoride -using anhydrous hydrogen fluoride as electrolyte- forming perfluoro-alkyl sulfonyl fluoride that is hydrolyzed in another reactor forming the analogous perfluoro-alkyl sulfonic acid. The raw material is n-paraffin or refinery fraction of n- paraffins that is sulfo-chlorinated using sulfur dioxide and chlorine forming alkyl sulfonyl chloride, which is further reacted with anhydrous hydrogen fluoride forming alkyl sulfonyl fluoride. The sulfo-chlorination reaction is carried out preferably inside bubble-column reactor. Optimum temperature range (40 ºC – 50 ºC) and pressure in the atmospheric range regarding the continuous venting to the phase separator. After leaving the sulfo-chlorination reactor, the effluent is cooled and sent to phase separator, the vapor phase containing hydrogen chloride, and traces of sulfur dioxide is sent to scrubber in which dilute hydrochloric acid wash captures hydrogen chloride byproduct and recover sulfur dioxide as sulfuric acid. perfluoro-octanesulfonic acid Appearance 25 °C , atm white corrosive solid faint irritating odor Relative Density 1.84 * (H2O = 1) Melting Point - 090 Boiling Point - 260 Flash Point - 0-- Synonyms PFOS foaming agent fire fighting foam impregnating agent textiles mist suppresant metal plating electrolysis emulsifier polytetrafluoroethylene perfluoro-elastomers synthetic rubber
  • 4. The liquid phase is sent to the fluorination reactor in which liquid effluent is reacted with liquid anhydrous hydrogen fluoride. Optimum temperature range (15 ºC – 20 ºC). The produced alkyl sulfonyl fluoride is sent to the electrolytic cell. The oxidation reaction or loss of electrons takes place on the anode producing perfluo-alkyl sulfonyl fluoride, and the reduction reaction or gain of electrons takes place on the cathode producing hydrogen byproduct. After leaving the electrolytic cell, the effluent is further hydrolyzed and separated using distillation, not difficult because of the comparatively distinctive boiling points of perfluoro-alkyl sulfonic acids. Practically, the yield decreases with increasing chain length.
  • 6. Process Description Production is based on electrochemical fluorination of alkyl acyl fluoride -using anhydrous hydrogen fluoride as electrolyte- forming perfluoro-alkyl acyl fluoride that is hydrolyzed in another reactor forming the analogous perfluoro-alkyl carboxylic acid. The raw material is n-carboxylic acid, that is chlorinated using thionyl dichloride forming alkyl acyl chloride and is further reacted with anhydrous hydrogen fluoride forming alkyl acyl fluoride. The chlorination reaction is carried out inside agitator-stirred tank or column reactor, in which thionyl chloride is introduced in portions to maintain temperature control. Optimum temperature range (40 ºC – 90 ºC) and pressure in the atmospheric range. During the reaction, sulfur dioxide is vented and sent to treatment unit. After leaving the reactor, the liquid effluent is separated in distillation column, not difficult because of the comparatively distinctive boiling points of carboxylic acid and the analogous acyl chloride. perfluoro-octanoic acid Appearance 25 °C , atm white corrosive solid pungent irritating odor Relative Density 1.80 * (H2O = 1) Melting Point - 054 Boiling Point - 192 Flash Point - 0-- Synonyms PFOA foaming agent fire fighting foam impregnating agent textiles mist suppresant metal plating electrolysis emulsifier polytetrafluoroethylene perfluoro-elastomers synthetic rubber
  • 7. The undesired sulfur dioxide is sent to treatment unit, in which it is chlorinated forming sulfuryl chloride that is further hydrolyzed into sulfuric acid and hydrogen chloride. The acyl chloride is sent to the fluorination reactor in which acyl chloride is reacted with liquid anhydrous hydrogen fluoride. The produced alkyl acyl fluoride is sent to the electrolytic cell. The oxidation reaction or loss of electrons takes place on the anode producing perfluo-alkyl acyl fluoride, and the reduction reaction or gain of electrons takes place on the cathode producing hydrogen byproduct. After leaving the electrolytic cell, the effluent is further hydrolyzed and separated using distillation.
  • 9. Alternative Process : Telomerization Production is based on telomerization , which is building macro-molecules through finite degree of polymerization of tetrafluoroethylene (telogen) with iodo-fluoro-alkane (taxogen) such as pentafluoro-iodoethane. The reaction is carried out in the gas phase inside tubular or packed bed reactor. Optimum temperature range (90 ºC – 180 ºC) and pressure in the range of 250 bar. After leaving the reactor, the effluent is further cooled and transferred to phase separator, the vapor phase containing slightly excess tetrafluoroethylene is recycled.The liquid phase containing perfluoro-alkyl acyl iodide is separated in distillation stages to recover traces of iodine. Treatment of perfluoro-alkyl acyl iodide with sulfur trioxide or chloro- sulfonic acid gives the carboxylic acid in good yield. Telomerization produces high purity completely linear compared to electrochemical fluorination.
  • 10. Process Description Production is based on electrochemical fluorination of 2- propoxypropionyl fluoride -using anhydrous hydrogen fluoride as electrolyte- forming perfluoro-propoxypropionyl fluoride that is hydrolyzed in another reactor forming the analogous perfluoro-alkyl carboxylic acid which is hexafluoropropylene oxide dimer acid. The raw material is propoxylated alcohol that is oxydized into carboxylic acid, which is further chlorinated using thionyl dichloride forming alkyl acyl chloride that is reacted with anhydrous hydrogen fluoride forming alkyl acyl fluoride. Proxylation is based on reacting propylene oxide and n- propanol over heterogenous catalyst. The process is carried out continuously in packed bed reactor by using clay catalyst as solid acidic catalyst, such catalyst can give low levels of impurities while remaining highly active. Optimum temperature range (70 ºC – 110 ºC) and pressure in the range of (15 bar – 50 bar). Higher (propylene oxide- propanol) ratios favor high yields of undesired heavy propoxylated alcohols, whereas lower ratios are used in this case to produce 2-propoxy propanol. hexafluoropropylene oxide dimer acid Appearance 25 °C , atm white corrosive liquid faint irritating odor Relative Density 1.75 * (H2O = 1) Melting Point < 025 Boiling Point - 188 Flash Point - 0-- Synonyms HFPO-DA foaming agent fire fighting foam impregnating agent textiles mist suppresant metal plating electrolysis emulsifier polytetrafluoroethylene perfluoro-elastomers synthetic rubber
  • 11. Converting alcohol into carboxylic acid is based on catalytic oxidation of using homogeneous catalyst composed of manganese or cobalt acetate and dissolved in an initial charge of propoxylated carboxylic acid (product). The reaction is carried out inside packed bed reactor or bubble column reactor. Optimum temperature range (30 ºC – 90 ºC) and pressure in the range of (2 bar – 20 bar). The vent gas is scrubbed with recirculated product stream to recover traces of the product. The reactor effluent containing crude propoxylated carboxylic acid is separated through distillation.
  • 13. The chlorination reaction is carried out inside agitator- stirred tank or column reactor reactor, in which thionyl chloride is introduced in portions to maintain temperature control. Optimum temperature range (40 ºC – 90 ºC) and pressure in the atmospheric range. During the reaction, sulfur dioxide is vented and sent to treatment unit. After leaving the reactor, the liquid effluent is separated in distillation column, not difficult because of the comparatively distinctive boiling points of propoxylated carboxylic acid and the analogous acyl chloride. The propoxylated alkyl acyl chloride is sent to the fluorination reactor in which it is reacted with liquid anhydrous hydrogen fluoride. Optimum temperature range (15 ºC – 20 ºC). The produced propoxylated alkyl acyl fluoride is sent to the electrolytic cell. The oxidation reaction or loss of electrons takes place on the anode producing perfluo-alkyl acyl fluoride, and the reduction reaction or gain of electrons takes place on the cathode producing hydrogen byproduct. After leaving the electrolytic cell, the effluent is further hydrolyzed and separated using distillation.