Technology Profile
Methionine Hydroxy Analog Production
By Intratec Solutions
M
ethionine is an essential
amino acid that is widely
used as an animal feed
additive, especially in the
poultry market. Hydroxy-methyl bu-
tyric acid, also known as methionine
hydroxy analog (MHA), is used in
animal nutrition as an equivalent to
methionine, since it is converted into
L-methionine by enzymes inside ani-
mals bodies.
The process
In the process described here, liquid
MHA is produced from 3-methylmer-
captopropionaldehyde (MMP) and
hydrogen cyanide. In the first step,
MMP is converted to hydroxy-methyl-
thiobutyronitrile (HMBN), which is then
hydrolyzed to MHA. Finally, MHA is re-
covered through solvent extraction.
Figure 1 is a simplified flow diagram of
this process.
HMBN synthesis. Liquid MMP is
continuously fed into the HMBN reac-
tor, while gaseous hydrogen cyanide
is fed through the reactor bottom.
The reaction of MMP and HCN is
catalyzed by a mixture of pyridine and
acetic acid. MMP is completely con-
verted, with high selectivity to HMBN,
and a few heavier byproducts. The ef-
fluent from this reactor is conducted
to a nitrogen-stripping column to re-
move unconverted hydrogen cyanide,
the HCN-free stream is then directed
to the MHA synthesis.
MHA synthesis. HMBN undergoes hy-
drolysis in three steps. At first, HMBN
is introduced into a continuously stirred
tank reactor (CSTR) along with pro-
cess water and a sulfuric acid stream.
Catalyst Off gas (to treatment)
1 2. Nitrogen stripper
MMP
2 ST
HCN
Nitrogen
Process water
Sulfuric acid
3 4
CW CW
FIGURE 1. Methionine hydroxy analog production from MMP and hydrogen cyanide
34
Natural gas/
Hydrogen cyanide
production
ammonia unit
Propylene
Acrolein
production
unit
Methyl mercaptan
Hydrogen sulfide/ production
methanol
unit
Main raw material Process Main product
FIGURE 2. Integrated process units for the production of methionine hydroxy analog
HMBN reacts with water to form an
amide (2-hydroxy-4-methylthiobutan-
amide), with sulfuric acid behaving as a
catalyst. The effluent from this reactor
and additional process water are intro-
duced into a second CSTR, operated
at higher temperatures. The amide is
hydrolyzed in a reaction with water and
sulfuric acid, forming MHA and ammo-
nium bisulfate. The effluent from this
second reactor is fed to a plug-flow re-
actor to guarantee complete hydrolysis
of the amide formed in the first step.
The resulting aqueous solution is sent
for purification.
Purification. MHA is extracted with
methyl isobutyl ketone (MIBK). The
extract, rich in MHA and solvent, is
steam-stripped. The water and sol-
vent are recovered from the top prod-
uct and a concentrated MHA stream
is recovered from the bottom. The
final product composition is correct-
ed with process water. The raffinate
from the extraction, mostly water and
ammonium bisulfate, is also steam-
stripped. The water is recovered from
the top and an aqueous solution con-
taining ammonium bisulfate is recov-
ered from the bottoms and disposed
of as waste.
7 ST
Extract
Process water
6 CW
5 CW
CHEMICAL ENGINEERING
MMP production MHA production Methionine
unit unit hydroxy analog
Economic performance
MHA production cost (including plant
operation, product sales, administra-
tion, R&D activities and depreciation)
is estimated at about $2,400 per ton
of product. The scope of this analy-
sis assumes a facility with capacity
to produce 160,000 metric tons per
year of MHA (88 wt.% liquid solution)
from HCN and MMP. The production
of these raw materials is usually in-
tegrated to the MHA process (Figure
2). The production cost was estimat-
ed based on data from the second
quarter of 2013 for a plant operating
in the U.S.
This column is based on Methio-
nine Hydroxy Analog Production Pro-
cess - Cost Analysis, a report pub-
lished by Intratec. It can be found at:
www.intratec.us/analysis/methionine-
production-cost.
Edited by Scott Jenkins
Editors note: The content for this column is supplied by
Intratec Solutions LLC (Houston; www.intratec.us) and ed-
ited by Chemical Engineering. The analyses and models
presented are prepared on the basis of publicly available
and non-confidential information. The content represents
the opinions of Intratec only. More information about the
methodology for preparing analysis can be found, along with
terms of use, at www.intratec.us/che.
1. HMBN reactor
3. First hydrolysis reactor
4. Second hydrolysis reactor
5. Finishing reactor
9
CW 6. Extraction column
8 7. Extract steam stripper
8. Decanter
ST
NH4HSO4 9. Raffinate steam stripper
solution 10. Cooling tower
MHA @ 88 wt% 11. Steam boiler
CW Cooling water
10 ST Steam
Solvent
ST 11
Raffinate
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