CA1042465A - Treatment of adiponitrile with strong-acid cation exchange resins - Google Patents
Treatment of adiponitrile with strong-acid cation exchange resinsInfo
- Publication number
- CA1042465A CA1042465A CA000234360A CA234360A CA1042465A CA 1042465 A CA1042465 A CA 1042465A CA 000234360 A CA000234360 A CA 000234360A CA 234360 A CA234360 A CA 234360A CA 1042465 A CA1042465 A CA 1042465A
- Authority
- CA
- Canada
- Prior art keywords
- adiponitrile
- cation exchange
- strong
- acid
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A process for reducing the amount of basic impurities, especially N-heterocyclic compounds, in adiponitrile is dis-closed. The process comprises treating adiponitrile with a strong acid cation exchange resin essentially in the absence of water. The strong-acid cation exchange resin used in the process is characterized by a macroreticular structure. The process is particularly useful in the purification of adiponitrile manufactured from adipic acid and ammonia.
A process for reducing the amount of basic impurities, especially N-heterocyclic compounds, in adiponitrile is dis-closed. The process comprises treating adiponitrile with a strong acid cation exchange resin essentially in the absence of water. The strong-acid cation exchange resin used in the process is characterized by a macroreticular structure. The process is particularly useful in the purification of adiponitrile manufactured from adipic acid and ammonia.
Description
~0~ 5 The presen-t invention rel~tes to the tre~tment o~
adiponitrile with strong-acid cation exchange re~ins and in particular to a process for reducing the amount o~ basic impurities in crude adiponitrile in whlch the crude adiponitrile is treated wl~h ~ strong-acid cation exchange resin essentially in the absence o~ water.
One o~ the mor~ important u~es of adiponitrile at the present tlme i~ in the manufac-ture of hexamethylene diamine~
mis diamine mag be used as a detergent, as an emulsi~ying agent or, in particular~ as an intermedla~e in the manu~acture of polymersO
A catalytic hydrogen~tion reaction is usually employed to convert adiponitr~le to hexamethylene diamineO
There are several methods for synthesizing adiponitrile.
: In particular, adlponitrile may be obtained b~ reacting adipic acid with ammonia in the presence o~ a dehydr~ting catalyst, ~or example5 by the techniques disclosed in U.S. Patent 2,200,734 o~
Arnold and Lazier which issued May 14, 1940 and in U.S~ Patent
adiponitrile with strong-acid cation exchange re~ins and in particular to a process for reducing the amount o~ basic impurities in crude adiponitrile in whlch the crude adiponitrile is treated wl~h ~ strong-acid cation exchange resin essentially in the absence o~ water.
One o~ the mor~ important u~es of adiponitrile at the present tlme i~ in the manufac-ture of hexamethylene diamine~
mis diamine mag be used as a detergent, as an emulsi~ying agent or, in particular~ as an intermedla~e in the manu~acture of polymersO
A catalytic hydrogen~tion reaction is usually employed to convert adiponitr~le to hexamethylene diamineO
There are several methods for synthesizing adiponitrile.
: In particular, adlponitrile may be obtained b~ reacting adipic acid with ammonia in the presence o~ a dehydr~ting catalyst, ~or example5 by the techniques disclosed in U.S. Patent 2,200,734 o~
Arnold and Lazier which issued May 14, 1940 and in U.S~ Patent
2,273,633 o~ M~ Lo Ao Fluchaire which issued February 17, 19420 .
Adiponltrile, especially adiponitrlle obtained from adipic acid contalns ~mpurities, some o~ which boil at temperature~ cloæe to the boiling point of adiponitrileO 2~Cyanocyclopentylidene- ~;
im~ne~ hereinafter sometimes re~erred to as CPI, is an example of such an impurityO Close boilin~ impurities frequentlg cannot be removed ef~iciently ln industrlal scale distillation columns. Impurities ln the adiponitrile may lead to impurities ~ ' ' , `
:. . , . :
:; . , ;. . . . . ~ , . ~ , in subsequent derivativ~s, in partlcular ln hexamethylene diamine~ that are difficult to removeO Failure to r~move these latter impuritie~ may result ln in~erlor and variable propertles, especlally in polymers ~anufactured using such impure hexamethylene diamineO Technique~ ~or the purific~tion of adlponltrlle are known in the artO For example, adlponitrile may be treated with a solid acidic catalyst in the presence o~ water and at a temperature of at least 140C to remove 2-cyanocyclopentylidene-imineO The solid acidic catalysts may be silica-alumina catalysts, crystalline aluminosilicates, boron phosphate or titania-alumina Such treatment is described in Canadian Patent 912,036 of BoJ~
Kershaw whlch issued October 10, 19720 Adlponitrile especially adiponitrile obtained from the reaction of adipic acid with ammonia may also contain impur-ities in the form of cyclic amines9 especiall~ N-heterocyclic compo~ndsO Examples of such impurities are 2-methyl-4-amino-5,6-trimethylene pyrimidine, hereinafter sometimes referred to ~s MAP, 2-amino~3,4,5,6-bis (trime~hylene) pyridine, hereinafter some~imes re~erred to a~ ABP, and 2 cyclopentyl-4-amino-5,6~tri-methylene pyrim~dine, hereinafter sometimes re~erred to as V~POSuch N-heterocyclic.compou~ds may cause problems in the hydrogen ation o~ adiponitrile to hexamethylene diamine or in the sub~
sequent puri~ication of hexamethylene dlamine.
It has now been found that basic lmpurities, especially N-heterocycllc co~pounds, may be remo~ed from crude adlponitrile b~ treating the adiponitrile in the absence o~ water with a strong-acid cation exchange resin havlng a macroreticular structure, such resins being discussed hereina~ter.
Accordingly, the present inventio~ provides a pro~
cess for reducing the amount o~ basic impurities in crude adiponitrile, said process comprising the steps of treating crude adiponitrile with a strong-acid cation exchange resin ~ 2 --.
.
-f~t;5 essenki~lly in -the ab~ence of` water Rnd ~t a temperature ln the range o~ from 20C up to the temperature at whlch degradation o~ the st.rong-acid cation exchange resin b~-comes signific~nt, said resin having a macroreticular structure and being in the hydrogen form, and separating adiponitrile therefromO
In a pre~erred embodiment of the proceæs o~ the present lnvention the te~perature is in the range 20C to 150C and es-pecially in the range 50C to 110Co In another embodiment the crude adiponitrile is essen~
~ially ~ree of ammoniaO
In a further embodiment the crude adiponitrlle is adiponitrile manu~actured from adipic acid and ammoniaO
Cation exchange resins are usually classified as being o~ three general types~ Strong-acid cation exchange resins ha~e a chemical activity similar to sulphuric acid and commercially are usually nuclear sulphonic ac~d or methylene sulphonic acid ~:
resins~ Intermed~ate~acld cation exchange resins have a chemical actlvity sim~lar to phosphoric acid and commercially are usually phosphonic acid, phosphonous ~cid or phosphoric acid resinsO
Weakacid c~tlon exchange reslns have a chemical activity simllar `
to acetic acid and commercially are usually carboxylic acid or phenolic resinsO
The cation exchang~ resins used in the proce~s of the presént in~ention are strong-acld resins which are capable of being used in anhydrous mediaO Such reslns are described in "AMBERLYST* 15 synthetlc resin cataly~ts", obtainable from Rohm and Haas~ as havlng a uni~ue porous structure sometimes, referred to as a "macroreticular" structure. The resins are used in the process in the hydrogen or acid form In the process of the present lnvention crude ~:
adiponitrile i5 treated with a strong-acid cation exchange resin ha~lng a macroreticular structure~ In the process the * de~otes trade mark ~ 3 Z~5 adiponitrile may be tre~ted by contacting the adiponitrlle and resin in a continuous process or in a batch process) the former being pre~erredO Preferably the ad:lponitrile is passed through a fixed bed o~ the ~trong-acid cation exchange resin. In ~
preferred embodlment the adiponitrile i~ adiponltrile manu factured from a~ipic acid and ammon'LaO
While the adiionitrile treated by the process of ~he present inventlon is described as "crude adiponitrile" the adiponitrile being treated is pre~erably adiponitrlle that has 10 been sub~ected to partial puri~ication e~g. by distillationO
The treatment of adiponitrile according to the procee3 of the present lnvention ls carried out essentially in the a~sence o~ wa~erO The temperature at which the adiponitrile is treated may be in the range of from about 20C to the temperature at which the strong-acid cation exchange resin exhibits signlflcant degradationO Such degradation may affect the properties of the cation exchange resin and/or the properties and especially the impurities in the adiponitrile after treatmentO
In partlcular, the adiponitrile after treatment may contain : 20 decomposit~on products of the cation exchange resinO The ~emperature at which decomposition of the cation exchange resin i may become signi~icant will depend on the actual resin being used and, in part, on the process conditlonsO Preferably the upper temperature limit is not in exces~ of 150C. Pre~erred temperature ranges are in the range 20 to 150C and in particular 50 to 110 C ,.
As stated above the treatment of the adiponitrile is i carried out essentially in the absence o~ waterO As used hereln the expression "treatment of adiponitrile essentially in the absence of wat~r" means the treatment o~ adiponitrlle containing less than about 0~1~ waterO Treat~ent of adiponitrile with a strong-acid cation exchange resin in the presence of wa~er may result in the hydrolysls o~ any 2-cyanocyclopentylideneimine ln the adiponitrile~ Such hydrolysis would result in the form~tion ,:
. ~ .
~ .: .. .
~ l) 4 ;~ 4--~; Sof ammcnla which would be absorbed by the resin thereby reducing the capacity of the resin ~or removing other amines The process o~ the present invention in which the adiponitrile is treated essentially in the absence of water may therefore o~er advantages over the treatment o~ adiponitrile wlth a strong-acid cation exchange resln in the presence of waterO
The pressura used ln the process of the present ~nvention is not criticalO The pressure will depend primarily on other process variables, for example, the temperature at which the process is operatedO
In a preferred embodiment of the process of the present invention the adiponitr~le is substantiall~ free of ammonia~
In the process of the present invention amines es~
pecially the aforementioned cyclic amines are removed from the adiponitrile by retention on the cation exchange resinO After a ! `
period o~ time it may become desirable to remove said amines from the cation exchange resin and thereby regenerate the resin for : further useO The resin may be regenerated ~y contacting with 20 an amount o~ a strong acid~ ~or example3 hydrochloric acid, ~ -.
that is in excess of the amount of acld required to convert ::
the re~in to its acid or hydrogen ~ormO The resin is used in the process o~ the present invention in its acid or hydrogen form~
After treatment with acid the resin should be washed with water and then driédO :~
Adlponitrile purified by the process described herein ~
is particul~rly useful in the manufacture o~ hexamethylene ~ :
diamlne using an iron catalyst as is described in Canadiarl patent application 234 ~56 o~ RoJ~ Kershaw filed on the same day as the present application The process o~ the present in~ention is illustrated by the following examplesO The adiponltrile used in the examples had been manufactured from adlpic acid and ammonia :... ,. . :., .. - ' . , ' ......... :, ' .
r~.. ~ ... . ; ; . ; ~ . . .
EXAMPLE I
____ To 50 ml of a crude adiponltrile havlng the ~ollowing composition:
: 2~cyanoc~clopent~1idenelmine (CPI) 0O15%
2-methyl 4-amino-5,6 trimethylene 0O028 pyrimldine (MAP) 2~amino~3,4,5~6-bis(trimethylene) 0O062 pyrldine (ABP) ~cyanovaleramide 0O13 water 001 were added 0O5 g of AMBERLYST 150 The re~ultant mixture was stirred for 20 minutes at ambient temperature and then analyzed by gas chromatographyO The results were as follows:
Time Impurity Levels in Adiponitrlle*
: CPI MAP ABP
O mLnO 0ol5 0~028 0~062 ~;
20 minO ~ 0O15 0~020 0,045 * in ~ weight/volumeO
E~AMPLE II
m e procedure of Example I was repeated at a temper- ;
ature o~ 100Co The re~ults were as follows: .
Tlme Impurity Level in Adiponitrile _ CPI MAP ABP
0 min~ 0O15 00~028 0O062 15 minO oo 12 0O013 0O027 35 minO oOo80 0O003 0O000 .
EXAMPLE III
- To demonstrate the e~fect of process variables the procedure of Example I was repeatsd at dlffere~t temperature~
and resin contentsO The results were as ~ollows:
- 6 ~
i . .
'''' ' :' ' " ' . ' ~4'~4f~5 Run No. 1 2 3 4 Temperature ( ~C ) 104 104 58 58 Resin (% by weight) loO 0~5 loO 0~5 Impurity Levels ( i) CPI 0 minutes 0O 15 0O 15 0.15 0.. 15 15 minutes oOog7 0013 0~130015 30 mlnutes 0O o84 0O 12 0.120O 15 60 minutes 00073 Ooll 0~0900~14 ( ii ) MAPO mlnutes 0O 028 0O 028 0. 028 0O 028 15 minutes OoOll 00017 0~0130~020 30 minutes 0O 005 0O 016 o, oO5 o 020 60 minutes OoOOl 00013 o,oo8o~olg - ( iii ) A~3PO minutes0. 0620O 062 0, 062 0O 062 -~ 15 minutes OoOl9 00035 o.o3600044 30 mi nutes NA 0O 030 0, 032 0, 041 . -60 minutes ()oO20 00024 0,.015 0~040 NA: not available :
.''...,.~ : , ..
' ~ ~
~ . .
. .
~'`
. . ~ ,. . , ~ , . . .
"
.... . . . .
Adiponltrile, especially adiponitrlle obtained from adipic acid contalns ~mpurities, some o~ which boil at temperature~ cloæe to the boiling point of adiponitrileO 2~Cyanocyclopentylidene- ~;
im~ne~ hereinafter sometimes re~erred to as CPI, is an example of such an impurityO Close boilin~ impurities frequentlg cannot be removed ef~iciently ln industrlal scale distillation columns. Impurities ln the adiponitrile may lead to impurities ~ ' ' , `
:. . , . :
:; . , ;. . . . . ~ , . ~ , in subsequent derivativ~s, in partlcular ln hexamethylene diamine~ that are difficult to removeO Failure to r~move these latter impuritie~ may result ln in~erlor and variable propertles, especlally in polymers ~anufactured using such impure hexamethylene diamineO Technique~ ~or the purific~tion of adlponltrlle are known in the artO For example, adlponitrile may be treated with a solid acidic catalyst in the presence o~ water and at a temperature of at least 140C to remove 2-cyanocyclopentylidene-imineO The solid acidic catalysts may be silica-alumina catalysts, crystalline aluminosilicates, boron phosphate or titania-alumina Such treatment is described in Canadian Patent 912,036 of BoJ~
Kershaw whlch issued October 10, 19720 Adlponitrile especially adiponitrile obtained from the reaction of adipic acid with ammonia may also contain impur-ities in the form of cyclic amines9 especiall~ N-heterocyclic compo~ndsO Examples of such impurities are 2-methyl-4-amino-5,6-trimethylene pyrimidine, hereinafter sometimes referred to ~s MAP, 2-amino~3,4,5,6-bis (trime~hylene) pyridine, hereinafter some~imes re~erred to a~ ABP, and 2 cyclopentyl-4-amino-5,6~tri-methylene pyrim~dine, hereinafter sometimes re~erred to as V~POSuch N-heterocyclic.compou~ds may cause problems in the hydrogen ation o~ adiponitrile to hexamethylene diamine or in the sub~
sequent puri~ication of hexamethylene dlamine.
It has now been found that basic lmpurities, especially N-heterocycllc co~pounds, may be remo~ed from crude adlponitrile b~ treating the adiponitrile in the absence o~ water with a strong-acid cation exchange resin havlng a macroreticular structure, such resins being discussed hereina~ter.
Accordingly, the present inventio~ provides a pro~
cess for reducing the amount o~ basic impurities in crude adiponitrile, said process comprising the steps of treating crude adiponitrile with a strong-acid cation exchange resin ~ 2 --.
.
-f~t;5 essenki~lly in -the ab~ence of` water Rnd ~t a temperature ln the range o~ from 20C up to the temperature at whlch degradation o~ the st.rong-acid cation exchange resin b~-comes signific~nt, said resin having a macroreticular structure and being in the hydrogen form, and separating adiponitrile therefromO
In a pre~erred embodiment of the proceæs o~ the present lnvention the te~perature is in the range 20C to 150C and es-pecially in the range 50C to 110Co In another embodiment the crude adiponitrile is essen~
~ially ~ree of ammoniaO
In a further embodiment the crude adiponitrlle is adiponitrile manu~actured from adipic acid and ammoniaO
Cation exchange resins are usually classified as being o~ three general types~ Strong-acid cation exchange resins ha~e a chemical activity similar to sulphuric acid and commercially are usually nuclear sulphonic ac~d or methylene sulphonic acid ~:
resins~ Intermed~ate~acld cation exchange resins have a chemical actlvity sim~lar to phosphoric acid and commercially are usually phosphonic acid, phosphonous ~cid or phosphoric acid resinsO
Weakacid c~tlon exchange reslns have a chemical activity simllar `
to acetic acid and commercially are usually carboxylic acid or phenolic resinsO
The cation exchang~ resins used in the proce~s of the presént in~ention are strong-acld resins which are capable of being used in anhydrous mediaO Such reslns are described in "AMBERLYST* 15 synthetlc resin cataly~ts", obtainable from Rohm and Haas~ as havlng a uni~ue porous structure sometimes, referred to as a "macroreticular" structure. The resins are used in the process in the hydrogen or acid form In the process of the present lnvention crude ~:
adiponitrile i5 treated with a strong-acid cation exchange resin ha~lng a macroreticular structure~ In the process the * de~otes trade mark ~ 3 Z~5 adiponitrile may be tre~ted by contacting the adiponitrlle and resin in a continuous process or in a batch process) the former being pre~erredO Preferably the ad:lponitrile is passed through a fixed bed o~ the ~trong-acid cation exchange resin. In ~
preferred embodlment the adiponitrile i~ adiponltrile manu factured from a~ipic acid and ammon'LaO
While the adiionitrile treated by the process of ~he present inventlon is described as "crude adiponitrile" the adiponitrile being treated is pre~erably adiponitrlle that has 10 been sub~ected to partial puri~ication e~g. by distillationO
The treatment of adiponitrile according to the procee3 of the present lnvention ls carried out essentially in the a~sence o~ wa~erO The temperature at which the adiponitrile is treated may be in the range of from about 20C to the temperature at which the strong-acid cation exchange resin exhibits signlflcant degradationO Such degradation may affect the properties of the cation exchange resin and/or the properties and especially the impurities in the adiponitrile after treatmentO
In partlcular, the adiponitrile after treatment may contain : 20 decomposit~on products of the cation exchange resinO The ~emperature at which decomposition of the cation exchange resin i may become signi~icant will depend on the actual resin being used and, in part, on the process conditlonsO Preferably the upper temperature limit is not in exces~ of 150C. Pre~erred temperature ranges are in the range 20 to 150C and in particular 50 to 110 C ,.
As stated above the treatment of the adiponitrile is i carried out essentially in the absence o~ waterO As used hereln the expression "treatment of adiponitrile essentially in the absence of wat~r" means the treatment o~ adiponitrlle containing less than about 0~1~ waterO Treat~ent of adiponitrile with a strong-acid cation exchange resin in the presence of wa~er may result in the hydrolysls o~ any 2-cyanocyclopentylideneimine ln the adiponitrile~ Such hydrolysis would result in the form~tion ,:
. ~ .
~ .: .. .
~ l) 4 ;~ 4--~; Sof ammcnla which would be absorbed by the resin thereby reducing the capacity of the resin ~or removing other amines The process o~ the present invention in which the adiponitrile is treated essentially in the absence of water may therefore o~er advantages over the treatment o~ adiponitrile wlth a strong-acid cation exchange resln in the presence of waterO
The pressura used ln the process of the present ~nvention is not criticalO The pressure will depend primarily on other process variables, for example, the temperature at which the process is operatedO
In a preferred embodiment of the process of the present invention the adiponitr~le is substantiall~ free of ammonia~
In the process of the present invention amines es~
pecially the aforementioned cyclic amines are removed from the adiponitrile by retention on the cation exchange resinO After a ! `
period o~ time it may become desirable to remove said amines from the cation exchange resin and thereby regenerate the resin for : further useO The resin may be regenerated ~y contacting with 20 an amount o~ a strong acid~ ~or example3 hydrochloric acid, ~ -.
that is in excess of the amount of acld required to convert ::
the re~in to its acid or hydrogen ~ormO The resin is used in the process o~ the present invention in its acid or hydrogen form~
After treatment with acid the resin should be washed with water and then driédO :~
Adlponitrile purified by the process described herein ~
is particul~rly useful in the manufacture o~ hexamethylene ~ :
diamlne using an iron catalyst as is described in Canadiarl patent application 234 ~56 o~ RoJ~ Kershaw filed on the same day as the present application The process o~ the present in~ention is illustrated by the following examplesO The adiponltrile used in the examples had been manufactured from adlpic acid and ammonia :... ,. . :., .. - ' . , ' ......... :, ' .
r~.. ~ ... . ; ; . ; ~ . . .
EXAMPLE I
____ To 50 ml of a crude adiponltrile havlng the ~ollowing composition:
: 2~cyanoc~clopent~1idenelmine (CPI) 0O15%
2-methyl 4-amino-5,6 trimethylene 0O028 pyrimldine (MAP) 2~amino~3,4,5~6-bis(trimethylene) 0O062 pyrldine (ABP) ~cyanovaleramide 0O13 water 001 were added 0O5 g of AMBERLYST 150 The re~ultant mixture was stirred for 20 minutes at ambient temperature and then analyzed by gas chromatographyO The results were as follows:
Time Impurity Levels in Adiponitrlle*
: CPI MAP ABP
O mLnO 0ol5 0~028 0~062 ~;
20 minO ~ 0O15 0~020 0,045 * in ~ weight/volumeO
E~AMPLE II
m e procedure of Example I was repeated at a temper- ;
ature o~ 100Co The re~ults were as follows: .
Tlme Impurity Level in Adiponitrile _ CPI MAP ABP
0 min~ 0O15 00~028 0O062 15 minO oo 12 0O013 0O027 35 minO oOo80 0O003 0O000 .
EXAMPLE III
- To demonstrate the e~fect of process variables the procedure of Example I was repeatsd at dlffere~t temperature~
and resin contentsO The results were as ~ollows:
- 6 ~
i . .
'''' ' :' ' " ' . ' ~4'~4f~5 Run No. 1 2 3 4 Temperature ( ~C ) 104 104 58 58 Resin (% by weight) loO 0~5 loO 0~5 Impurity Levels ( i) CPI 0 minutes 0O 15 0O 15 0.15 0.. 15 15 minutes oOog7 0013 0~130015 30 mlnutes 0O o84 0O 12 0.120O 15 60 minutes 00073 Ooll 0~0900~14 ( ii ) MAPO mlnutes 0O 028 0O 028 0. 028 0O 028 15 minutes OoOll 00017 0~0130~020 30 minutes 0O 005 0O 016 o, oO5 o 020 60 minutes OoOOl 00013 o,oo8o~olg - ( iii ) A~3PO minutes0. 0620O 062 0, 062 0O 062 -~ 15 minutes OoOl9 00035 o.o3600044 30 mi nutes NA 0O 030 0, 032 0, 041 . -60 minutes ()oO20 00024 0,.015 0~040 NA: not available :
.''...,.~ : , ..
' ~ ~
~ . .
. .
~'`
. . ~ ,. . , ~ , . . .
"
.... . . . .
Claims (6)
1. A process for reducing the amount of basic impurities in crude apiponitrile,said process comprising the steps of treating crude adiponitrile with a strong-acid cation exchange resin essentially in the absence of water and at a temperature in the range of from 20°C up to the temperature at which degradation of the strong-acid cation exchange resin becomes significant, said resin having a macroreticular structure and being in the hydrogen form, and separating adiponitrile therefrom.
2. The process of Claim 1 in which the adiponitrile is treated with the resin in the substantial absence of ammonia.
3. The process of Claim 2 in which the adiponitrile is adiponitrile manufactured from adipic acid and ammonia.
4. The process of Claim 3 in which the temperature is in the range 20°C to 150°C.
5. The process of Claim 3 in which the temperature is in the range 50°C to 110°C.
6. The process of any one of Claim 1, Claim 3, and Claim 5 in which the crude adiponitrile has been subjected to distillation prior to treatment with the resin.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000234360A CA1042465A (en) | 1975-08-26 | 1975-08-26 | Treatment of adiponitrile with strong-acid cation exchange resins |
| IT2584376A IT1065070B (en) | 1975-08-26 | 1976-07-29 | PROCESS FOR THE PRODUCTION OF HEXAMETHYLENE DIAMINE |
| GB2643777A GB1539436A (en) | 1975-08-26 | 1976-08-17 | Process for purifying adiponitrile |
| GB3427076A GB1539435A (en) | 1975-08-26 | 1976-08-17 | Process for the manufacture of hexamethylene diamine |
| FR7625712A FR2322127A1 (en) | 1975-08-26 | 1976-08-25 | PERFECTED PROCESS FOR THE PRODUCTION OF HEXAMETHYLENE DIAMINE FROM CRUDE ADIPONITRILE |
| DE19762638510 DE2638510A1 (en) | 1975-08-26 | 1976-08-26 | IMPROVED PROCESS FOR THE PREPARATION OF HEXAMETHYLENEDIAMINE |
| FR7706940A FR2334664A1 (en) | 1975-08-26 | 1977-03-09 | METHOD FOR REDUCING THE QUANTITY OF N-HETEROCYCLIC AMINE IN CRUDE ADIPONITRILE |
| US05/858,661 US4146555A (en) | 1975-08-26 | 1977-12-08 | Process for purifying adiponitrile |
| US05/858,663 US4147717A (en) | 1975-08-26 | 1977-12-08 | Process for purifying adiponitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000234360A CA1042465A (en) | 1975-08-26 | 1975-08-26 | Treatment of adiponitrile with strong-acid cation exchange resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042465A true CA1042465A (en) | 1978-11-14 |
Family
ID=4103918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000234360A Expired CA1042465A (en) | 1975-08-26 | 1975-08-26 | Treatment of adiponitrile with strong-acid cation exchange resins |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1042465A (en) |
-
1975
- 1975-08-26 CA CA000234360A patent/CA1042465A/en not_active Expired
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