CA1175861A - Process for liberating dialdehyde from an aqueous solution - Google Patents
Process for liberating dialdehyde from an aqueous solutionInfo
- Publication number
- CA1175861A CA1175861A CA000437505A CA437505A CA1175861A CA 1175861 A CA1175861 A CA 1175861A CA 000437505 A CA000437505 A CA 000437505A CA 437505 A CA437505 A CA 437505A CA 1175861 A CA1175861 A CA 1175861A
- Authority
- CA
- Canada
- Prior art keywords
- percent
- dialdehyde
- weight
- aqueous solution
- mixture
- 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
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 title abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229920005862 polyol Polymers 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 150000003077 polyols Chemical class 0.000 claims abstract description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical group O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 13
- -1 aliphatic polyol Chemical class 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims 1
- 230000000994 depressogenic effect Effects 0.000 abstract description 3
- 238000010790 dilution Methods 0.000 abstract description 3
- 239000012895 dilution Substances 0.000 abstract description 3
- 229960000587 glutaral Drugs 0.000 description 11
- 230000008014 freezing Effects 0.000 description 6
- 238000007710 freezing Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 101150034533 ATIC gene Proteins 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
- 240000004543 Vicia ervilia Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000009428 plumbing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Described herein is a process for rapidly obtaining a stable freeze point depressed aqueous solution comprising a dialdehyde and an aliphatic alcohol and/or polyol by adding thereto a catalytic amount of a strong acid. Also included herein is a method for liberating the dialdehyde in the aqueous solution by dilution with water and the addition of a catalytic amount of a strong acid.
Described herein is a process for rapidly obtaining a stable freeze point depressed aqueous solution comprising a dialdehyde and an aliphatic alcohol and/or polyol by adding thereto a catalytic amount of a strong acid. Also included herein is a method for liberating the dialdehyde in the aqueous solution by dilution with water and the addition of a catalytic amount of a strong acid.
Description
This invention is di~ected to a process for sapidly obtaining a stable ~reeze point depressed aqueous solution comp~ising a dialdehyde and an .. alip~atic alcoho} ~n~/or polyol by adding ~here~o a catalytic amount o~ a strong acid. Also, included herein is a method for liberating the d:ialdehyde ~n the aqueous solution by dilution with water and the addition o a catalytic a~unt of a strong acid.
Aqueous ~olution~ of ~lutaraldehyde ~re well kno~n commerei~lly ~v~lable materi81~ u~eful for k~ll$ng or lnhibiting lche gsowth ~f micrs:)org8.n~6ms.
~e8e aqueou~ ~olutions of glutaraldehyde have been u~ed to ~ontrol the grawth o: bacteri~ in ~ nun~er s:~f different env~ronment3d For ex~ , glu~ar~Lldehyde 801utions have been used to di~infeet ~edical and ~urgic~l s~pplies and househo~d ob,3eces. Fur~herg a~ de~cribed in U.S. Pate~ 2~801~16 ~lu~r~ldehyde ~vlut~ons have be~n u~ed to control bac~er~a in w~er .. flooding operations ~or ~he ~econdary recovery ~f oil and u~ed ~o prevent corrosion and plugg~ng of iron equipment due to ~he action of bacteri~ or~ge vessels and as~oclated plumbing and equ~pme~t~ Thu~, ~t can be seen that there a~e o~C~610~S ~hen glu~ar~l-dehyde ~o$utions ~re ~ored out of door~ a~d may ~e ~ub~ected to ~reezing condieio~. The freezi~g poi~t of ~ 25 percent aqueou~ ~olution of glut~raldehyte ~ ou~ 22~. ~herefore, lt ~ould be des~able ~nder these cond~tio~ to ~urthes d~pre3s ~he ~reezing pol~t o ~he aqueou~ ~olutisn of g~utassld~h~d~. ~owever9 ~y ~ddi~lve ~o ~he ~queous glutaraldehyt~ ~olu~o~
~ch c~uld depre~ ~he free~B po~e o~ ~h~ ~olu~a .
must not dec~ease t~e che~ical or biolog:lcal activity o~ ~e solution At time o~ use and n~tst be one which ~a~ntains the freezing polnt at the desired tempera-eure. ~ha~ is, the.addi~ive ~hould be one which i9 able to maintain the desired temperature over extendad periods of time. For example, bot~ alcohvls ~nd I
glycols, such as meth~nol and ethylenle glyco~ are known to react with glutaraldehyde so tha~ even though addition of methanol or e~ylene glycol to an aqueous solution of glutaraldehyde initially depr~sses the freezlng point, upon storage) ~he free~ing point ri.se~
as the alcohol and glycol react with ~he glutaraldehyde to fo~m a mixture containing acetal linkages. There-~ore, it i~ ~çsirablé to have a 3table ~ixed reezing point.
DESCRIPTION OF THE INVENTION
I~ has been found ~hat the addition of a cataly~ic amount of a strong acid ~o an aqueou~ æolu-tion compris~ng a dialdehyde and an aliphatic alcohol and/or polyol free~e point depre~sant rapidly catalyzes the formation of an equilibrium mix~ure of the dial-dehyde, acetal, and freeze point depress~n~, which equilibrium mixture has a stable and fixed freezing point.
I~ has also been found that in order to rapldly and efficien~ly llberate the dialdehyde for acti~e chemic~l or b~.o~ogical reactions, dilution o~ ~e equllibrium mixture with water and the ~urt~er ~dd~.t~on o~ a c~taly~ic ~mount o~ a strong acld i~
necessary, 5~6~
The aliphatic alcohols which may ~e used as ~ree~e point depressants herein contain from 1 to 4 ca~bon ato~s, such as methano~, ethémol and the llke, and ~ixtur~s there.of~ T~e pre~erred alcohol i~
methanol.
The aliphatic polyols which may be employed ~n this in~ention as ~reezing point depressants contain from 2 to 6 carbon atoms, and include ethylene glycol, propylene glycol, glycerol and the like, and mixtures thereof. The preferred polyol ls ethyl~ne glycol.
It is understood that one or more aliphatic alco~ols may be mixed wlth one or more aliphatic polyo~s.
The acids which are suitable for use in this invention are acids capable of achieving ~n aqueous pH below abou~ 3.0, preferably below about 2.0, and include pho~phorir acid, hydrochloric acid, sulfuric acid, trifluoromethylsulfonic acid,para- oluenesulfonic acid, ' as well as supported acid catalyst~, ~uch as ~mberlyst~
whlch ~s a supported arylsulfonic acid (sold by Ro~
& Haas Company~ and Nafion which ~s a supported fluoro-~ulfonic acid (sold by E. I. duPont de Nemours Co.),.
In order to achieve a ~table freeze point depressed produc~, ~he aqueous solution generally contaln~ from about 0.1 ~o about 50 percent by weight.
o~ the dialde~yde; from about 5 to about ~0 percent by weigh~ of the aleohol and~os glycol,with the ~emainder of ~he ~olutio~ belng water 3UC~ that the total ~olutioR i~ 100 percent by weighe. A preferred ~olution contain~ ~ percene by weight of dialdehyd~, R ~ R ~ ~ -7~
30 percent by weight o~ alcohol and/or glycol and 45 percent ~y weight o water.
In order to rapidly and efficiently liberate the dlaldehyde for ac~lve chem~cal or biolo~7ical reac-~tions, the aqueous ~olu~ion should contain from about O. 01 to about 10 percent o the d~aldehyde and a cataly-tic amount of an acid, and may contain up to about 40 percent by w ight o the alcohol and/or polyol, with the remainder of ~he solution being water such that the total 301u~ion i8 100 percent by welg,ht.
The solul:ions may contain o~her additi~Te~
8UC~ as coloran~s, sur~actants, chelating agents, p~ bu~er~,and the l~ke.
EXAMPLES
The ~ollowing exa~ples ~erve to give specific ~llustratlons of the practice of this invention but they are not intended în any way to limit the ~cope o~ this invention.
CONTROL A
The freezing point of a mixture of ~5 percent by weight of glutaraldehyde and 75 pe~cent by welght of water ls 22~F (as determined by the procedure as ~et forth in ASTM D-1177-65).
CONTR~L B
, The following ingredient w2re mixed:
25 percent by ~eight of glutaraldehyde, ~5 percent by weight of methanolJ a~d -50 percen~ by weight of water.
- - The ~eez~ng poi~t o~ the m~xture w~ -20.15~F
and ~he pH was ab9ut 4Ø A~ter ~torage for 55 da~y~
.. . . .. ..... . .. .. . .. . .. . ... . .... ... . .. ..
t~5~ L
at a~out ~5C, the ~reezing point of the mixture was measured and found to be -9.5F.
CO~lTROL G
The f~llowing lngredients were mixed: . . . .
25 percent by weight o glut~raldehyde, 25 percent by weight of ethylene glycol, and 50 percent by weight of water.
The freezing point o~ the mixture was -14.0F
and the pH was about 4Ø After storage or 55 days at about 25C, the freezing point of the mixture was measured ~nd ound to be -7. 5~F, EXA~LE 1 The following ingredients were mixed:
25 percent by welght of glutaraldehyde, 25 percent by weight of methanol, and 50 perrent by weight of water.
A one percent solution of phosphoric acid was added ~o the solutio~ un~il a pH of 1 to 2 was achie~ed.
The freezing point of the equilibrium mixture was -9.0~F.
_ _ The following ingredients were mLxed:
- 25 percent by weight of gl~taraldPhyde, ~5 percent by weight of eehylene glycol, and 50 percent by weight of water.
A one pe~een~ ~olution o~ phosphor~c acid was ~ddet to ehe ~olution until ~ p~ o~ 1 ~o ~ was a~hievQd.
~he ~reezing point o~ t~e mixture was 3~F.
The aqueous equilibrium m~xtures ~n Exampl2s 1 . . . . .. . .... . . .. .. . . . .
5~
and ~ were ~onmed ~n less than about 3 hours. These e~u~librium mixtures are able to mantain the stated ~reezing point over long per~ods of time, even after G months of storage.
~n contradistinct~on, the ~ree2ing points of the mixtures of Controls ~ and B varied~ significantly a~ter only 55 ~ays and up t~ three m~nths may be required for the solu~ion ~o achieve e~uil:Lbrium.
~x~n~ 6 3 10 7 In these examples, the follo~ing ingredients were mixed:
25 perce~t by weight of glutaraldehyde, 30 perc~nt by weight of methanol, ~nd 45 percent by weight of water.
Thi8 mixture was stored for about 6 months.
The ~inal equilibrium of the mix~ure had been reached ~t this point in time. Thls mlxture was diluted to 0.1% of theoretical glutaraldehyde. T~ ~Farate por-tion~ of the mixture was added a one p~rcent ~olution o~ phosphoric acid until the desired pH was achieved.
The percent of glu~araldehyde recovered from the mixlture at various times and pH values is shown in Table I.
The glutaralde~yde le~els were determinet by gas ehromatography.
~ TABLE I
Time P~ -~x~ple ~ ) : 2 3 4 5 I~
3 l,0 ~0% 77% 5~%
4 3.0 ~3Z 7~
i.0 g37O 81% ~%
24~ ~7~ 93% ~9% 37% 44Z
7 48.0 9~ ~3% 73Z 37% 44%
,P~`~
In these Examples, the followlng ingredients were mixed:
~5 percent by weight of glutaraldehyd~J
. 30 percent by weight of ethylene glycol, and 45 percent by weight o~ water.
This mixture was stored for 6 months. The ~inal equilibrium of ~he mixture had been reached.
This mixture was diluted to 0.1% of theoretical glu-taraldehyde. To separate portions of the mixture was added a one percent 801ution o phosphoric acid until the desired pH was achieved. The percent of glutar-~ldehyde recovered from the mixture a~ var~us times and pH values is shown in Table X~. The glutaraldehyde levels were determ med ~y gas chromatography.
TABLE II
T~me H
Example ~ ) Z 3 ~~
8 1.0 - - 50% -
Aqueous ~olution~ of ~lutaraldehyde ~re well kno~n commerei~lly ~v~lable materi81~ u~eful for k~ll$ng or lnhibiting lche gsowth ~f micrs:)org8.n~6ms.
~e8e aqueou~ ~olutions of glutaraldehyde have been u~ed to ~ontrol the grawth o: bacteri~ in ~ nun~er s:~f different env~ronment3d For ex~ , glu~ar~Lldehyde 801utions have been used to di~infeet ~edical and ~urgic~l s~pplies and househo~d ob,3eces. Fur~herg a~ de~cribed in U.S. Pate~ 2~801~16 ~lu~r~ldehyde ~vlut~ons have be~n u~ed to control bac~er~a in w~er .. flooding operations ~or ~he ~econdary recovery ~f oil and u~ed ~o prevent corrosion and plugg~ng of iron equipment due to ~he action of bacteri~ or~ge vessels and as~oclated plumbing and equ~pme~t~ Thu~, ~t can be seen that there a~e o~C~610~S ~hen glu~ar~l-dehyde ~o$utions ~re ~ored out of door~ a~d may ~e ~ub~ected to ~reezing condieio~. The freezi~g poi~t of ~ 25 percent aqueou~ ~olution of glut~raldehyte ~ ou~ 22~. ~herefore, lt ~ould be des~able ~nder these cond~tio~ to ~urthes d~pre3s ~he ~reezing pol~t o ~he aqueou~ ~olutisn of g~utassld~h~d~. ~owever9 ~y ~ddi~lve ~o ~he ~queous glutaraldehyt~ ~olu~o~
~ch c~uld depre~ ~he free~B po~e o~ ~h~ ~olu~a .
must not dec~ease t~e che~ical or biolog:lcal activity o~ ~e solution At time o~ use and n~tst be one which ~a~ntains the freezing polnt at the desired tempera-eure. ~ha~ is, the.addi~ive ~hould be one which i9 able to maintain the desired temperature over extendad periods of time. For example, bot~ alcohvls ~nd I
glycols, such as meth~nol and ethylenle glyco~ are known to react with glutaraldehyde so tha~ even though addition of methanol or e~ylene glycol to an aqueous solution of glutaraldehyde initially depr~sses the freezlng point, upon storage) ~he free~ing point ri.se~
as the alcohol and glycol react with ~he glutaraldehyde to fo~m a mixture containing acetal linkages. There-~ore, it i~ ~çsirablé to have a 3table ~ixed reezing point.
DESCRIPTION OF THE INVENTION
I~ has been found ~hat the addition of a cataly~ic amount of a strong acid ~o an aqueou~ æolu-tion compris~ng a dialdehyde and an aliphatic alcohol and/or polyol free~e point depre~sant rapidly catalyzes the formation of an equilibrium mix~ure of the dial-dehyde, acetal, and freeze point depress~n~, which equilibrium mixture has a stable and fixed freezing point.
I~ has also been found that in order to rapldly and efficien~ly llberate the dialdehyde for acti~e chemic~l or b~.o~ogical reactions, dilution o~ ~e equllibrium mixture with water and the ~urt~er ~dd~.t~on o~ a c~taly~ic ~mount o~ a strong acld i~
necessary, 5~6~
The aliphatic alcohols which may ~e used as ~ree~e point depressants herein contain from 1 to 4 ca~bon ato~s, such as methano~, ethémol and the llke, and ~ixtur~s there.of~ T~e pre~erred alcohol i~
methanol.
The aliphatic polyols which may be employed ~n this in~ention as ~reezing point depressants contain from 2 to 6 carbon atoms, and include ethylene glycol, propylene glycol, glycerol and the like, and mixtures thereof. The preferred polyol ls ethyl~ne glycol.
It is understood that one or more aliphatic alco~ols may be mixed wlth one or more aliphatic polyo~s.
The acids which are suitable for use in this invention are acids capable of achieving ~n aqueous pH below abou~ 3.0, preferably below about 2.0, and include pho~phorir acid, hydrochloric acid, sulfuric acid, trifluoromethylsulfonic acid,para- oluenesulfonic acid, ' as well as supported acid catalyst~, ~uch as ~mberlyst~
whlch ~s a supported arylsulfonic acid (sold by Ro~
& Haas Company~ and Nafion which ~s a supported fluoro-~ulfonic acid (sold by E. I. duPont de Nemours Co.),.
In order to achieve a ~table freeze point depressed produc~, ~he aqueous solution generally contaln~ from about 0.1 ~o about 50 percent by weight.
o~ the dialde~yde; from about 5 to about ~0 percent by weigh~ of the aleohol and~os glycol,with the ~emainder of ~he ~olutio~ belng water 3UC~ that the total ~olutioR i~ 100 percent by weighe. A preferred ~olution contain~ ~ percene by weight of dialdehyd~, R ~ R ~ ~ -7~
30 percent by weight o~ alcohol and/or glycol and 45 percent ~y weight o water.
In order to rapidly and efficiently liberate the dlaldehyde for ac~lve chem~cal or biolo~7ical reac-~tions, the aqueous ~olu~ion should contain from about O. 01 to about 10 percent o the d~aldehyde and a cataly-tic amount of an acid, and may contain up to about 40 percent by w ight o the alcohol and/or polyol, with the remainder of ~he solution being water such that the total 301u~ion i8 100 percent by welg,ht.
The solul:ions may contain o~her additi~Te~
8UC~ as coloran~s, sur~actants, chelating agents, p~ bu~er~,and the l~ke.
EXAMPLES
The ~ollowing exa~ples ~erve to give specific ~llustratlons of the practice of this invention but they are not intended în any way to limit the ~cope o~ this invention.
CONTROL A
The freezing point of a mixture of ~5 percent by weight of glutaraldehyde and 75 pe~cent by welght of water ls 22~F (as determined by the procedure as ~et forth in ASTM D-1177-65).
CONTR~L B
, The following ingredient w2re mixed:
25 percent by ~eight of glutaraldehyde, ~5 percent by weight of methanolJ a~d -50 percen~ by weight of water.
- - The ~eez~ng poi~t o~ the m~xture w~ -20.15~F
and ~he pH was ab9ut 4Ø A~ter ~torage for 55 da~y~
.. . . .. ..... . .. .. . .. . .. . ... . .... ... . .. ..
t~5~ L
at a~out ~5C, the ~reezing point of the mixture was measured and found to be -9.5F.
CO~lTROL G
The f~llowing lngredients were mixed: . . . .
25 percent by weight o glut~raldehyde, 25 percent by weight of ethylene glycol, and 50 percent by weight of water.
The freezing point o~ the mixture was -14.0F
and the pH was about 4Ø After storage or 55 days at about 25C, the freezing point of the mixture was measured ~nd ound to be -7. 5~F, EXA~LE 1 The following ingredients were mixed:
25 percent by welght of glutaraldehyde, 25 percent by weight of methanol, and 50 perrent by weight of water.
A one percent solution of phosphoric acid was added ~o the solutio~ un~il a pH of 1 to 2 was achie~ed.
The freezing point of the equilibrium mixture was -9.0~F.
_ _ The following ingredients were mLxed:
- 25 percent by weight of gl~taraldPhyde, ~5 percent by weight of eehylene glycol, and 50 percent by weight of water.
A one pe~een~ ~olution o~ phosphor~c acid was ~ddet to ehe ~olution until ~ p~ o~ 1 ~o ~ was a~hievQd.
~he ~reezing point o~ t~e mixture was 3~F.
The aqueous equilibrium m~xtures ~n Exampl2s 1 . . . . .. . .... . . .. .. . . . .
5~
and ~ were ~onmed ~n less than about 3 hours. These e~u~librium mixtures are able to mantain the stated ~reezing point over long per~ods of time, even after G months of storage.
~n contradistinct~on, the ~ree2ing points of the mixtures of Controls ~ and B varied~ significantly a~ter only 55 ~ays and up t~ three m~nths may be required for the solu~ion ~o achieve e~uil:Lbrium.
~x~n~ 6 3 10 7 In these examples, the follo~ing ingredients were mixed:
25 perce~t by weight of glutaraldehyde, 30 perc~nt by weight of methanol, ~nd 45 percent by weight of water.
Thi8 mixture was stored for about 6 months.
The ~inal equilibrium of the mix~ure had been reached ~t this point in time. Thls mlxture was diluted to 0.1% of theoretical glutaraldehyde. T~ ~Farate por-tion~ of the mixture was added a one p~rcent ~olution o~ phosphoric acid until the desired pH was achieved.
The percent of glu~araldehyde recovered from the mixlture at various times and pH values is shown in Table I.
The glutaralde~yde le~els were determinet by gas ehromatography.
~ TABLE I
Time P~ -~x~ple ~ ) : 2 3 4 5 I~
3 l,0 ~0% 77% 5~%
4 3.0 ~3Z 7~
i.0 g37O 81% ~%
24~ ~7~ 93% ~9% 37% 44Z
7 48.0 9~ ~3% 73Z 37% 44%
,P~`~
In these Examples, the followlng ingredients were mixed:
~5 percent by weight of glutaraldehyd~J
. 30 percent by weight of ethylene glycol, and 45 percent by weight o~ water.
This mixture was stored for 6 months. The ~inal equilibrium of ~he mixture had been reached.
This mixture was diluted to 0.1% of theoretical glu-taraldehyde. To separate portions of the mixture was added a one percent 801ution o phosphoric acid until the desired pH was achieved. The percent of glutar-~ldehyde recovered from the mixture a~ var~us times and pH values is shown in Table X~. The glutaraldehyde levels were determ med ~y gas chromatography.
TABLE II
T~me H
Example ~ ) Z 3 ~~
8 1.0 - - 50% -
2~ 9 1.67 77% 54% - - -1~ 2.17 81% 66% - ~ ~
11 3.0 - _ _ 59% ~7%
12 24.0 99% 76% 54% - ~
13 72.0 ~ 1% 5270 ~.
11 3.0 - _ _ 59% ~7%
12 24.0 99% 76% 54% - ~
13 72.0 ~ 1% 5270 ~.
Claims (4)
1. A process for liberating a dialdehyde from an aqueous equilibrium mixture comprising a dialdehyde, acetal, and an aliphatic alcohol and/or polyol by first diluting the mixture with water and then adding a catalytic amount of a strong acid.
2. A process as defined in claim 1 wherein the dialdehyde is glutaraldehyde.
3. A process as defined in claim 1 wherein the aliphatic alcohol is methanol.
4. A process as defined in claim 1 wherein the aliphatic polyol is ethylene glycol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000437505A CA1175861A (en) | 1981-11-30 | 1983-09-23 | Process for liberating dialdehyde from an aqueous solution |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000391189A CA1173058A (en) | 1980-12-30 | 1981-11-30 | Process for obtaining a stable depressed freeze point aqueous solutions of dialdehydes |
| CA000437505A CA1175861A (en) | 1981-11-30 | 1983-09-23 | Process for liberating dialdehyde from an aqueous solution |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000391189A Division CA1173058A (en) | 1980-12-30 | 1981-11-30 | Process for obtaining a stable depressed freeze point aqueous solutions of dialdehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1175861A true CA1175861A (en) | 1984-10-09 |
Family
ID=25669496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000437505A Expired CA1175861A (en) | 1981-11-30 | 1983-09-23 | Process for liberating dialdehyde from an aqueous solution |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1175861A (en) |
-
1983
- 1983-09-23 CA CA000437505A patent/CA1175861A/en not_active Expired
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