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Sep. 5, 2013
(72) Inventor.
Publicatm classi?ca?m
(5 1)
Int. Cl.
C07C 53/122
(200601)
(52) U-s- C1
CPC .................................. .. C07C 53/122 (2013.01)
(21)
(22) Flled'
(57)
Apr' 12 2013
.
(63)
ABSTRACT
propionate.
Sep. 5, 2013
US 2013/0231504 A1
[0003]
acrolein.
[0005]
starting materials.
[0007]
Without di?iculty.
[0008]
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glycerol.
materials.
[0023]
Propionic acid/AA
Ex-glycerol process
<5%
>10%
<0.1%
>0.5%
Ex-propylene process
[0017] The acetic acid and the propionic acid cause di?i
culties for the acrylic acid, in particular because they are not
converted during the polymerization process; they are satu
rated and thus cannot be polymerized. Depending on the
polymerization process involved and the applications tar
geted for the polymer, these impurities may remain in the
?nished product and risk conferring undesirable corrosive
streams: the heavy fraction from (4), heavy fraction from (5)
or light fraction from (6), in order to isolate crystals of puri
?ed acrylic acid and a solution of mother liquors depleted in
acrylic acid
[0032] catalytic hydrogenation of the mother liquors iso
lated in the fractional crystallization stage in the pres
ence of molecular hydrogen in order to form a propionic
acid solution
[0035]
[0020]
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recover in value the second stream and thus delimit the losses
1.2><10_12.
[0038]
[0049]
ried out over solid acid catalysts. The catalysts Which are
suitable are materials used in a gaseous or liquid reaction
[0052]
promoter, such as Au, Ag, Cu, Pt, Rh, Pd, Ru, Sm, Ce, Yt, Sc,
Sep. 5, 2013
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stages, for example the Water resulting from stages (1') and
tion catalyst.
[0058]
one element chosen from the list Mo, V, W, Re, Cr, Mn, Fe,
Co, Ni, Cu, Zn, Sn, Te, Sb, Bi, Pt, Pd, Ru and Rh, present in
[0059]
Sep. 5, 2013
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Weight).
[0069] In an alternative embodiment, this column can be
coupled to a second column for recovery of the solvent, so as
but also at the top and at various points of the columns and
devices, so as to provide continuous and homogeneous re?ux
of solution rich in polymerization inhibitors over all the parts
of the devices. Generally, they are conveyed in solution in a
[0076]
[0070]
bottom comprises acrylic acid freed from the bulk of the light
compounds. The column top stream, Which is rich in acetic
acid and formic acid, can optionally be additionally treated in
order to recover, in a second column in series, the small
amounts of acrylic acid entrained With the column top stream.
[0078]
receiver.
[0082]
[0073]
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being possible for the mother liquors from this third step to be
recycled in the charge of the 2nd step and the pure product
step.
[0090]
tion step fed solely With a puri?ed stream from the n- 1 step.
[0086]
the process in a loWer -2 step. The steps -1, -2, and the
approximately 3 MPa;
[0096] by heterogeneous gas-phase catalysis over a
in propionic acid.
[0087]
mately 6 atm;
[0097] by heterogeneous catalysis over a palladium cata
lyst applied in the form of a liquid palladium salt solu
tion absorbed on a porous support, such as silicic acid or
Sep. 5, 2013
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[0098]
rated by reference.
[0099]
by Weight.
[0104]
(co)polymers.
[0105] The application of a stage of fractional crystalliZa
tion of the acrylic acid combined With the hydrogenation of
the mother liquors isolated at the end of this stage exhibits the
ex-glycerol process.
[0106] The process for the manufacture of propionic acid
according to the invention is illustrated by the folloWing
examples.
EXAMPLE 1
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This tube is fed at the top in the form of a liquid ?lm Which
1 .2><104 Pa.
[01 13]
[0121]
EXAMPLE 3
(1)
[0118] The stream of acrylic acid of technical quality
obtained in example 2 is subjected to a series of puri?cation
and concentration steps by fractional crystallization, as
described in the present application. The arrangement used is
Sep. 5, 2013
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EXAMPLE 4
(2)
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139]
steel (length of the tube 100 cm, internal diameter 2.5 cm,
Wall thickness 4 mm) Was packed over its entire length With
EXAMPLE 5
temperature of 185 C.
[0142] 10 g/h of the residual mother liquors Were intro
mother liquors.
[0143] The mixture of acrylic acid and of molecular hydro
gen exiting from the evaporator Was immediately conveyed,
from the bottom upWards, through the jacketed tubular reac
tor. The end of the latter is at atmospheric pressure. The
temperature in the middle of the reactor is approximately
220 C. The unreacted acrylic acid and the propionic acid
produced Were recovered by condensation in a separator at
100 C.
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
Sep. 5, 2013
US 2013/0231504 A1
[0174]
[0171]
by condensation in a separator at 10 C.
[0173]