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TECHNOLOGICAL INSTITUTE OF THE PHILIPPINES
363 P. CASAL ST., QUIAPO, MANILA
CHEMICAL ENGINEERING DEPARTMENT DEPARTMENT EQUIPMENT DESIGN
PRODUCTION OF METHYL ETHYL KETONE
Submitted by:
ABUEL, Johannah Jane C. ANG, Queenie Queenie Anne Anne F. F. LAYAG, LAYAG, Vinen! Ja"i##e Ja" i##e C. PITO$AL, Anna Te%e&a S.
Submitted to:
En'%. Jo(e!h $a"i&
No)e"*e% +, -+
Production of Methyl Ethyl Ketone by Direct oxidation Hoechst-Wacker Process
I.
Process Description
An aqueous solution of PdCl2 and CuCl2 is used as catalyst. Methyl Ethyl Ketone (MEK) formation had already been observed in the reaction between nbutene and aqueous !alladium chloride. "he de#ree of o$idation lost by the !alladium must then be restored so that the followin# reaction sequence is involved% a) Methyl Ethyl Chloride !roduction nbutene & !alladium chloride & water MEK & !alladium & hydrochloric acid nC' & PdCl2 & 2* C'* & Pd & 2Cl b) *$idation of !alladium by cu!ric chloride +n the ,ac-eroechst !rocess metallic !alladium is reo$idi/ed by CuCl2 which is then re#enerated with o$y#en% Pd & 2CuCl2 PdCl2 & 2CuCl 2Cl & 012 *2 2* & Cl2 2CuCl & Cl2 2CuCl2 "he nbutene and o$y#en are char#ed into the lower !art of the reaction tower. *n the whole the followin# overall reaction ta-es !lace% nbutene & o$y#en methyl ethyl -etone nC' &012*2 C'* to which the catalyst solution ta-es is also added and is circulated via the se!aratin# vessel !reheated to the same tem!erature and o!eratin# at 0.2 -Pa absolute. "he e$it stream leavin# at 02C are flashed at 3 - Pa absolute to enable the se!aration of the reactants and !roducts of the reaction medium in #aseous form and the re#eneration of the catalyst -e!t in the liquid !hase. "he reaction !roducts are se!arated by coolin# and washin# with water the unconverted #as is returned to the reactor after the condition of ma-eu! hydrochloric acid and chlorides to offset any losses.. "he or#anic com!ounds stri!!ed in the #as !hase are recoververd by water scrubbin# in an absor!tion column o!eratin# aat atmos!heric !ressure around 3*C and recycled with the catalyst solution. Crude MEK obtained durin# washin# of the reaction !roducts is distilled in two sta#es. "he first sta#e is an e$tractive distillation with water in which li#hts ends havin# lower boilin# !oints than MEK are se!arated at the to! while water and hi#herboilin# by!roducts are withdrawn to#ether with MEK at the bottom. +n the second column MEK is !urified by fractional distillation.
II.
Aailability of !a" Materials
+n direct o$idation of nbutanes by oechst,ac-er !rocess o$y#en is transferred in a homo#enous !hase on to nbutanes usin# redo$ salt !air PdCl2 1 CuCl2.
4!littin# of 2!henyl butane hydro!ero$ide into !henol and methy ethyl -etone this intermediate bein# itself obtained by the al-ylation of ben/ene by means of nbutenes. A number of differences nevertheless a!!ear between the !urification schemes of acetone and methyl ethyl -etone. "he e$istence of a water1methyl ethyl -etone heteroa/eotro!e com!licates the se!aration of the !roducts. (Chauvel 5 6efebvre 078).
III.
#ostin$
Methyl ethyl -etone is a mature !roduct with most of its a!!lications only #rowin# slowly. 9e#ionally the Euro!ean and :.4. mar-ets are flat while future #rowth will be concentrated in Asia. "he Chinese mar-et is the main driver and demand here will rise by 8;<1year. Asian methyl ethyl -etone (MEK) !rices fell by more than '< in the three months to midAu#ust as a result of wea- consumer demand. Prices in northeast Asia settled at =083>0;31tonne C?9 (cost 5 frei#ht) down from =@>@@1tonne in midMay. 9ecord hi#h !rices in A!ril followin# an e$tended outa#e at a 0; tonne1year a!anese facility led end users from downstream sectors such as !olyurethane (P:) in- and coatin#s to switch to more affordable substitutes.
4tron# Chinese e$!orts also hel!ed offset the decline in su!!ly from a!an. Consum!tion levels are li-ely to remain wea- in the nearterm as !rices have not fallen to levels low enou#h for end users to consider switchin# bac- to MEK. owever the start of the !ea- !roduction season in the downstream P: sector in 4e!tember may hel! to su!!ort !rices. (Beow 2;)
I%.
Efficiency
A soluble mi$ture of PM* o$ides and an acetonitrile li#and is used to im!rove activity and selectivity with a yield of 3 to < efficiency. ("a-ao-a 07;2).
%.
Manufacturability and &ustainability
+n nature Methyl ethyl -etone (MEK) is made by some trees. +t is also found in small amounts in some fruits and ve#etables. Manmade MEK is released into the air from car and truc- e$hausts. MEK worldwide is !rimarily !roduced with nbutene12butene as the raw material. A newer technolo#y involves the direct o$idation of nbutene is solution usin# !alladium and cu!ric chloride as catalysts. "he main disadvanta#e of this !rocess is the formation of chlorinated butanones and bbutryaldehyde and corrosion caused due to free acids. (Chemical ,ee-ly 20)
Production of Methyl Ethyl Ketone by %apor Phase Dehydro$enation of '-butanol Process
I.
Process Description
A reactor in which the butanol is dehydrated to !roduce MEK and hydro#en accordin# to the reaction% CH 3 CH 2 CH 3 CHOH →CH 3 CH 2 CH 3 CO + H 2
"he conversion of alcohol to MEK is !er cent and the yield can be ta-en as 0 !er cent. A coolercondenser in which the reactor off#ases are cooled and most of the MEK and unreacted alcohol are condensed. "wo e$chan#ers are used but they can be modelled as one unit. *f the MEK enterin# the unit ' !er cent is condensed to#ether with 72 !er cent of the alcohol. "he hydro#en is non condensable. "he condensate is fed forward to the Dnal !uriDcation column. An absor!tion column in which the uncondensed MEK and alcohol are absorbed in water. Around 7 !er cent of the MEK and alcohol can be considered to be absorbed in this unit #ivin# a 0 !er cent w1w solution of MEK. "he water feed to the absorber is recycled from the ne$t unit the e$tractor. "he vent stream from the absorber containin# mainly hydro#en is sent to a are stac-. An e$traction column in which the MEK and alcohol in the solution from the absorber are e$tracted into trichloroethylane ("CE). "he rafDnate water containin# around .3 !er cent w1w MEK is recycled to the absor!tion column. "he e$tract which contains around 2 !er cent w1w MEK and a small amount of butanol and water is fed to a distillation column . A distillation column which se!arates the MEK and alcohol from the solvent "CE. "he solvent containin# a trace of MEK and water is recycled to the e$traction column. A second distillation column which !roduces a !ure MEK !roduct from the crude !roduct from the Drst column. "he residue from this column which contains the bul- of the unreacted 2butanol is recycled to the reactor. II.
Aailability of !a" Materials
MEK is !re!ared by va!or !hase dehydro#enation of 2butanol. A 2 ste! !rocess from butanes which are first hydrated to #ive 2butanol is used. "he dehydro#enation of 2butanol is an e$othermic reaction (30 -1-mol). "he reaction is as follows%
"he equilibrium constant for 2butanol can be calculated as follows%
,here% " F reaction tem!erature K K! F equilibrium constant bar
"he MEK concentration in the reaction mi$ture increases and reaches its ma$imum at a!!ro$imate @3GC. Co!!er /inc or bron/e are used as catalysts in #as !hase dehydro#enation. 4ecbutyl alcohol is dehydro#enated in a multi!le tube reactor the reaction heat bein# su!!lied by heat transfer oil. "he reaction !roducts leave the reactor as #as and are s!lit into crude MEK and hydro#en on coolin#. "he hydro#en is !urified by further coolin#. "he crude MEK is se!arated from uncreated reactants and by!roducts by distillation.
III.
#ostin$
4everal economic studies have been !erformed on the !roduction of butanol (traditional AHE fermentation) from corn whey !ermeate and molasses. Iew develo!ments in !rocess technolo#y for butanol !roduction could allow for a si#nificant reduction in the !rice of butanol. Petrochemical industries #ave ca!acity to reduce the !rice of butanol.
I%.
Efficiency
ave a hi#her conversion of 2butanol of about 73< and hi#h selectivity of MEK of about 73 mole <. %.
Manufacturability and &ustainability
Commercially used catalysts are reactivated by o$idation with a lon#er catalyst life after @ to 8 months use and have a better yield com!are to other !rocesses. "hey have a life e$!ectance of several years.
Production of Methyl Ethyl Ketone fro( n-butane by )i*uid Phase +xidation
I.
Process Description
"he !rocess starts with the nbutane and com!ressed air1o$y#en bein# fed to the reactor."he followin# reaction will ta-e !lace in the reactor
n −butane+ oxygen→aceticacid + MEK + other by − products + water
+n the reactor air is bubbled throu#h the reactant solution at 03⁰C to 223⁰C with !ressures of about 3.3 MPa. ?rom the reactor the !roduct mi$ture is !assed throu#h heat e$chan#ers coolers and then throu#h a decanter where the va!ors containin# crude acetic acid and various by!roducts includin# methyl ethyl -etone are se!arated from unreacted nbutane and inert #ases. "hen they are stri!!ed or flashed to remove dissolved butane and inert #ases and is sent to the !urification section. "he unreacted nbutane and inert #ases are sent to a se!arator for removal1recyclin# of unreacted hydrocarbons. +n the !urification section three!hase distillation columns are used with strai#ht e$traction to recover MEK.
II.
Aailability of !a" Materials
"he liquid !hase of butane is one of the most efficient modern !etrochemical !rocesses. "he !roducts of this !rocess are acetic acid methyl ethyl -etone (MEK) methyl acetate and other substances which are im!ortant chemicals. (M.J. Huly#in 0783) urin# this !rocess the main raw materials are butane and o$y#en. Hutane comes from natural #as which is colorless odorless and sha!eless in its natural form. "his ty!e of #as is relatively ine$!ensive to mine and !roduce since it is e$tremely abundant in many !arts of the world. *$y#en is a hi#hly reactive element and is ca!able of combinin# with most other elements it is the third most abundant element in the universe and ma-es u! nearly 20< of the earthLs atmos!here. *$y#en accounts for nearly half of the mass of the earthLs crust two thirds of the mass of the human body and nine tenths of the mass of water. 6ar#e amounts of o$y#en can be e$tracted from liquefied air throu#h a !rocess -nown as fractional distillation. *$y#en can also be !roduced throu#h the electrolysis of water or by heatin# !otassium chlorate (KCl*@).
III.
#ostin$
Source: U.S. Energy Information Administration based on Bloomberg Financial-reported prices at Mont Belvieu !e"as.
I%.
Efficiency
Production of Methyl Ethyl Ketone via liquid !hase o$idation will have low conversion and very low yield which will lead to low !roduction efficiency. (Arora 5 4harma 20)
%.
Manufacturability and &ustainability
*ne way to !roduce methyl ethyl -etone is by liquid !hase o$idation of nbutane. +n this !rocess MEK is !roduced as a by!roduct in the liquid !hase o$idation of nbutane to acetic acid. Auto$idation of n butane ta-es !lace in the liquid !hase accordin# to the radical mechanism yieldin# MEK as an intermediate and acetic acid as end!roduct with mass ratio .2%0. by noncataly/ed liquid !hase o$idation at 0oC and 3@ bars with remi$in#. Continuous o$idation under !lu# flow conditions at 03oC 83 bars and a residence time of 2; minutes forms MEK and acetic acid at a mass ratio of @%0. "his !rocess has sli#ht economic advanta#e over the dehydro#enation of 2butanol. Hut the -ey factor is availability and !rice of butane. +t also has a very low ener#y consum!tion and very hi#h economic feasibility which will result to a sustainable manufacturin# !rocess. (Arora 5 4harma 20)
