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English Description:

Technical feld

The invention belongs to the application technical feld o catalytic hydrogenation,specifc in order to prepare the para-aminomethyl benzoic acid catalytic

hydrogenation as relieving the acidic method o hemal ring under the amiable

condition.

Background Art

Tranexamic acid hether anti-orm, to aminomethyl hexahydrobenzoate, it can

through to bind to the reversibility o !,"-diaminocaproic acid is blocked on

plasminogen member, thus produced and resisted fbrinogenolytic e#ects, the

e#ective extensive situation used or hemorrhage, usually used in air passage,

hemorrhage o digestive tract, capillary hemorrhage, surgical operative

hemorrhage,etc..

$elieving the acidic synthetic method o hemal ring mainly has amphi, a is a methyl

acrylate method, produce tranexamic acid through a series o reactions by methyl

acrylate and chloro-butadiene% Another kind is a para-aminomethyl benzoic acid

method, passed the catalytic hydrogenation, transormed and produces tranexamic

acid by para-aminomethyl benzoic acid.Because should use hypertoxic cyanide in

the methyl acrylate method, mainly use the para-aminomethyl benzoic acid method

to produce tranexamic acid industrially.

The para-aminomethyl benzoic acid method is produced in the tranexamic acid

process, the catalytic hydrogenation is the most important step, to aminomethyl

hexahydrobenzoic acid to the ammonia Toluol frst one that got sym-orm and anti-

orm through the catalytic hydrogenation, transorm the sym-orm to aminomethyl

hexahydrobenzoic acid and turn into the anti-orm to aminomethyl

hexahydrobenzoic acid, i.e. tranexamic acid.&atalyst that catalyzed is usually

precious metal such as 't, $h, $u.

() *+*!+ uses $u catalyst, supports $u on inert supports such as alumina,

diatomaceous earth, activated carbon, barium sulate precipitated, calciumcarbonate, $u content in catalyst is -/ t0.At 1/ 2 o temperature, hydrogen

pressure // kg3cm!4eave and react, the transormation e5ciency o para-

aminomethyl benzoic acid is //0, it is +0 to the ormic yield o cyclohexyl group

o aminomethyl.4ast catalyst or +/"! times 6',ill 1 g para-aminomethyl

benzoic acid, ". g 789, // ml 9!10 $u-& 8 and !1 g adds into high pressure

autoclave, at +/ 2 o temperature, hydrogen pressure +/ kg3cm!4eave and react,

the product gets *.1 g to aminomethyl hexahydrobenzoic acid ater processing.

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:B !/;1 uses 'd, 't, $h mixed catalyst, separately 'd, 't, $h supports on the

activated carbon to make 10 'd-&, 10 't-&, 10 $h-& catalyst, add these three

kinds o catalyst mixing into high pressure autoclave, add para-aminomethyl

benzoic acid, ater, hydrochloric acid, reaction temperature is /-"/ 2, hydrogen

pressure -/ kg3cm!,$eaction " h, about ;/0 to the ormic yield o cyclohexylgroup o aminomethyl.

6' 1;/*!;; uses $h catalyst, supports $h on the activated carbon to get fnal

product 10 $h-& catalyst, reaction temperature is / 2 s, hydrogen pressure */

kg3cm!,$eaction * h, reaches +/0 to the ormic yield o aminomethyl cyclohexen.

ater ?=/.

/1=/.1"=**,it add para-aminomethyl benzoic acid and ater into at reaction tank, it

is i you can@t don, add by suluric acid not to stir, heating make dissolve, add

platinum dioxide, eliminate pot inect the hydrogen and begin to react behind the

air.About / 2, hydrogen pressure /.1-.1 kg3cm!The reaction relieves to no longer

hydrogen uptake o the amount o theory reached o hydrogen uptake.liminate my

hydrogen, flter reaction solution, take out platinum black.9eat fltrate to +/ 2,

neutralize ith barium hydroxide, come p9?-.1.Ater leting standstill, flter o#

the barium sulate precipitated.>ash the flter residue ith ater, mix fltering,

ash liCuids, get the sym-orm liCuid to aminomethyl cyclohexanecarboxylic acid

Dconcentration concentrates to carboxylic benzylamine reaction solution to 1 liters

or every / grammoleE ater concentrating.The ratio o components o the

conversion process is to the aminomethyl cyclohexanecarboxylic acid sym-orm

liCuid DvE= Barium hydroxide DE= >ater DvE= thanol DvE ?=!.=."=".".)ym-ormliCuid and barium hydroxide ill be added into the reaction tank to aminomethyl

cyclohexanecarboxylic acid, airtight, heat it up to !// 2, the pressure is ;-!/

kg3cm!,$eact or hours.The reaction is fnished, it is cold to "/-/ 2, ater and

heat up to +/ 2, neutralize to p9 ith suluric acid D*/0E ?1.1!-1.1".)tand or

more than ! hours, flter, the flter cake is ashed ith ater.

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An obect o the present invention is to provide a kind o reaction time short, the

para-aminomethyl benzoic acid o high productive rate method or preparing

tranexamic acid o catalytic hydrogenation, use high active hydrofning catalyst at

the same time, make para-aminomethyl benzoic acid prepare the catalytic

hydrogenation in the tranexamic acid process and go on under the reactioncondition that more :entle.

To achieve the above-mentioned obect, the technology solution o the invention is,

use 't-

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!. Because the catalyst activity is high, only need to react or !- hours, the

transormation e5ciency o para-aminomethyl benzoic acid can be more than +;0,

and can be more than +10 to the aminomethyl cyclohexanecarboxylic acid yield

and shorten the reaction time, improve the unit productive rate.

*. Gt is milder that para-aminomethyl benzoic acid catalyzes the reaction condition

adopted in the hydrogenation process, reaction temperature is */-"/ 2, hydrogen

pressure /.*-/."

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time 3 h+ the paraaminomethl ben/oic acid transformation e8cienc is

96."; 7ake to aminomethl cclohexanecarboxlate ,ntil alkalineearth

metal catal/e+ 220 -+ the in)ersion of cong,ration gets tranexamic acid

,nder 2.57a condition.

Embodiment 3

#ccelerant preparation: 0.135g H2t!l"#nd 0.g !o %&'3(2Dissol)e into

30ml *ater+ impregnate 1g acti)ated carbon in this sol,tion+ impregnate

12 h+ heat it to 100 -+ drip !H3!''&a sol,tion+ red,ces and nishes

postcooling+ lter+ #,eo,s+ make t!o! catalst.

!ataltic hdrogenation: #dd the 0.3 abo)ementioned catalst+ 1 g para

aminomethl ben/oic acid+ 30 ml deioni/ed *ater into high press,re

a,tocla)e+ 0." g H24'+#irtight+ )ac,,mi/e ,ntil0.0? 7pa+ replace air

t*ice *ith nitrogen+ hdrogen exchange nitrogen t*ice+ the reaction

temperat,re of heating is to 0 -+ hdrogen press,re 0.5 7a+ reaction

time h+ the paraaminomethl ben/oic acid transformation e8cienc is

9?."; 7ake to aminomethl cclohexanecarboxlate ,ntil alkalineearth

metal catal/e+ 220 -+ the in)ersion of cong,ration gets tranexamic acid

,nder 2.27a condition.

Embodiments

#ccelerant preparation: 0.135g H2t!l"#nd 0.03g >,!l3Dissol)e into 30ml

*ater+ impregnate 1g acti)ated carbon in this sol,tion+ impregnate 13 h+

heat it to 95 -+ drip &a'H sol,tion and glacial acetic acid+ red,ces andnishes postcooling+ lter+ #,eo,s+ make t>,! catalst.

!ataltic hdrogenation: #dd 0.3 g catalst+ 1 g paraaminomethl ben/oic

acid+ 30 ml deioni/ed *ater into high press,re a,tocla)e+ 0." g

H24'+#irtight+ )ac,,mi/e+ replace the air+ reaction temperat,re is 30 -+

hdrogen press,re 0. 7a+ reaction time h+ the paraaminomethl

ben/oic acid transformation e8cienc is 99.5.

Embodiment 5

#ccelerant preparation: 0.135g H2t!l"#nd 0.g !e %&'3(3Dissol)e into

30ml *ater+ impregnate 1g acti)ated carbon in this sol,tion+ impregnate

11 h+ heat it to 105 -+ drip hdra/ine hdrate+

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H24'+#irtight ++@ac,,mi/e+ replace the air+ reaction temperat,re is "0 -+

hdrogen press,re 0.5 7a+ reaction time 2 h+ the paraaminomethl

ben/oic acid transformation e8cienc is 99.".