CA2061718A1 - Method for inhibiting color contamination in ethanolamine compounds - Google Patents
Method for inhibiting color contamination in ethanolamine compoundsInfo
- Publication number
- CA2061718A1 CA2061718A1 CA 2061718 CA2061718A CA2061718A1 CA 2061718 A1 CA2061718 A1 CA 2061718A1 CA 2061718 CA2061718 CA 2061718 CA 2061718 A CA2061718 A CA 2061718A CA 2061718 A1 CA2061718 A1 CA 2061718A1
- Authority
- CA
- Canada
- Prior art keywords
- ethanolamine
- compound
- compounds
- per million
- amine
- 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.)
- Abandoned
Links
Abstract
ABSTRACT
The present invention is directed towards methods for inhibiting color formation in ethanolamine compounds. Color formation and contamination can be inhibited by adding an effective amount of an amine compound.
The present invention is directed towards methods for inhibiting color formation in ethanolamine compounds. Color formation and contamination can be inhibited by adding an effective amount of an amine compound.
Description
2~ 7:1~
METHOD FOR INHIBITING COLOR CONTAMINATION
IN ETHANOLAMINE COMPOUNDS
FIELD OF THE INVENTION
The present invention is directed to a method of inhibiting color formation and contamination in ethanolamine compounds. More specifically, the present invention is directed to a method of using amine compounds to inhibit the formation of oxygen containing compound impurities which cause color contamination in ethanolamine compounds.
BACKGROUND OF tHE INYENTION
Ethanolamine compounds, which include monoethanolamine, diethanolamine and triethanolamine, are produced commercially by reacting ethylene oxide, ammonia and water in a tubular reactor.
Oftentimes, the compounds generated by this method exhibit an undesirable color and color instability developed over a period of time. Nickel contained in the process system metallurgy is thought to catalyze dehydrogenation reactions of by-product ethylene glycol. It is thought that these reactions form oxygen containing carbonyl compounds such as aldehydes and ketones.
The aldehyde compounds can undergo the aldol-condensation reactions in the process system environment. Nickel may also catalyze the direct decomposition of the ethanolamine compounds, further forming carbonyl compounds.
2~71~
One theory postulates that these condensation polymer-ization contaminants thus formed can cause color contamination problems in the finished ethanolamine product.
Avoidance of color contamination increases the value of the ethanolamine compound to the producer and minimizes the off-specification product manufactured.
SUMMARY OF THE INVENTION
The present invention provides for a method for inhibiting color formation in ethanolamine compounds comprising adding to said ethanolamine compounds an effective amount for the purpose of an amine compound of the formula R"
, N - (CH2)x - R' R
wherein R is H or OH; R' is - NH (CH2CH2NH)yH
where y is an integer from about 0 to about 20, r\ r~ ~
--N NH, --N N - (CH2)2NH2. --N\__/N - (CH2)3 NH2 OH
CH3 - CH, - , --N((CH2 CH2)NH2)2, OH
- NH(cH2cH2NH)zcH2 ~ where z is 0,1,2,3,4, R''' 2~7~
OH
R" is H or (CH2)X-R' or -CH2 ~ and R''' OH OH
R''' is ~ CH2NHcH2cH2NHcH2 ~ O J
R R
and x is about 1 to about 3.
While effective in all ethanolamine compounds, the method of the present invention is particularly effective at inhibiting color formation in monoethanolamine, diethanolamine and triethanolamine.
The present method entails ensuring that the amine compounds are present in the ethanolamine reactor effluent.
DESCRIPTION OF THE RELATED ART
United States Patent 4,952,301, Awbrey, August 1990, dis-closes a method of inhibiting the formation of polymeric fouling deposits formed during the caustic washing of hydrocarbons. This method employs the use of an ethylenediamine compound.
2~7~8 United States Patent 3,819,710, Jordan, June 1974, discloses a process for improving the color and color stability of ethanolamine compounds. This process comprises hydrogenation of crude mono - , di and triethanolamines using selected catalysts at specific temperatures and pressures.
United States Patent 4,673,762, Paslean et al., June 1987, discloses a method for decolorizing ethanolamine compounds. This method employs adding to the ethanolamine compound an alkyleneoxide such as ethylene oxide.
Japanese Patent Publication No. 1977 - [Showa 52]-28,770 discloses a method of decoloring ethyleneamines and alkanolamines.
This method is accomplished by heat treatment of the amine compound in the presence of hydrogen and a catalyst. The catalyst can be selected from a nickel-type, cobalt-type or nickel-cobalt-mixed type hydrogenation catalyst.
European patent registration A1 0,004,015 discloses a process for the manufacture of colorless ethanolamines. This process entails carrying out the ethylene oxide, ammonium, water reaction in the presence of phosphorous acid or hypophosphorous acid or their compounds.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides for a method for inhibiting color formation in ethanolamine compounds comprising adding to said 2 ~ ~ 1 r7 ethanolamine compounds an effective amount for the purpose of an amine compound of the formula R"
, N - (CH2)x - R' R
wherein R is H or OH; R' is - NH (CH2CH2NH)yH
where y is an integer from about O to about 20, /~\ / \ ~
--N NH, --N N - (CH2)2NH2, --N\~_ /N - (CH2)3 NH2 OH
CH3 - CH, - , --N((CH2 CH2)NH2)2 OH
- NH(CH2CH2NH)zcH2 ~ where z is 0,1,2,3,4, R''' OH
R" is H or (CH2)X-R' or -CH2 ~ and R''' OH OH
R''' is ~ CH2NHCH2CH2NHcH2 R R
and x is about 1 to about 3.
2~ 7~ ~
Of these compounds, tetraethylenepentamine is preferred.
In addition, exemplary compounds include diethylenetriamine and triethylenetetramine. The tetraethylenepentamine is preferred as it possesses a higher boiling point than the other two compounds and thus can inhibit color formation at higher temperatures.
These amine compounds are also ashless compounds. This makes their use desirable as industry is moving away from ash containing compounds due to the clean-up costs involved.
These color inhibiting compounds can be added to the ethanolamine compounds as neat materials or in solution form.
The preferred method of addition is as an aqueous solution.
The treatment should be added to the ethanolamine in sufficient quantity to ensure there is enough of the amine compound present to react with all the undesirable carbonyl contaminants. Treatment dosages in the range of from about 1 part per million to about 10,000 parts per million parts of ethanolamine compound may be employed. Preferably, the amine compound is added in a range of about 5 parts per million to about 5000 parts per million parts of the ethanolamine compound to be treated.
The invention will be further illustrated by the following examples which are intended merely for purpose of illustration and are not to be regarded as limiting the scope of the invention or the manner in which it may be practiced.
2 0 ~
EXAMPLES
Examp~e 1 In a 17 ml test tube, 10.0 ml of triethanolamine was added. 40 ul of treatment (160 ul of 25% solution) was also - 5 added along with a piece of steel. The remaining 7 ml of air space was then purged with argon for 60 seconds and then the cap was securely fastened. The test tube was then placed in a sili-cone oil bath at the appropriate temperature for the specified time indicated in the table. The time in days represents how many days since the reaction was started. The yellow to brown colors were then compared visually. The results of this first test appear in Table I.
TABLE I
Triethanolamine color development 310 stainless steel 4,000 parts per million actives Days Since Reaction Temperature ofOrder of Color Started Bath (C) (Darkest to Lightest) 5 144 HS > TETA > NP > Blank, Blank No SS
7 204 HS > Blank No SS > TETA, NP, Blank 8 204 Blank No SS > HS > Blank > NP > TETA
9 204 Blank No SS > HS > Blank > NP > TETA
HS = Hydroxylamine sulfate NP = Nonylphenol TETA = Triethylenetetramine Blank No SS - Blank run with no stainless steel present.
2a~7~
The results of this test indicate that triethylene-tetramine is more effective at inhibiting color formation than the blank runs over a greater length of time and temperature.
Example 2 The procedure of example 1 was followed here. These results are shown in Table II.
TABLE II
Triethanolamine color development 4000 parts per million active at 168C
Days Since Reaction Order of Color Started(Darkest to Liqhtest) With 310 SS Present 2 HS > TETA > EDA > Blank > NP > DETA = TEPA
4 HS > TETA > EDA > Blank > NP > DETA = TEPA
Without 310 SS Present 2 HS > EDA > NP > Blank = TETA = DETA = TEPA
4 HS > Blank > NP > EDA = TETA = DETA = TEPA
HS = Hydroxylamine Sulfate EDA = Ethylenediamine NP = Nonylphenol : TETA = Triethylenetetramine DETA = Diethylenetriamine TEPA = Tetraethylenepentamine 21~ 1 7~
The polyamines diethylenetriamine and tetraethylenepent-amine were always less colored than the blanks. The polyamines ethylenediamine and triethylenetetramine proved better than the blanks at longer heating periods with no steel present.
Example 3 The procedure of example 1 was followed. The tubes were then wiped clean and inserted into a Hach spectrophotometer set at 410nm and calibrated with an unheated, untreated triethanolamine sample. The results are presented in Table III as % transmittance (%T)-TABLE III
Triethanolamine Color Development 4000 parts per million active at 190C
No 310 SS present %T %T %T %T
Treatment 24 Hours 48 Hours 62 Hours 24 Hours ---------Argon Purged----------- Air Purged None 3.5,3.0 1.0,2.5 0.7 0.2 EDA - 64.0 - 4.0 DETA 73.0 63.0 - 7.5 2~ 7~8 TABLE III (Cont'd) %T %T %T %T
Treatment 24 Hours 48 Hours 62 Hours 24 Hours ---------Argon Purged----------- Air Purged .
TEPA 58.5 - 11.0 AEP 44.0 BISAPP 66.5 TREN 27.0 HPHA 25.0 MD 35.0 EDA = Ethylenediamine DETA = Diethylenetriamine TETA = Triethylenetetramine TEPA = Tetraethylenepentamine AEP = N-(2-aminoethyl)piperazine BISAPP = N,N'-bis(3-aminopropyl)piperazine TREN = Tris(2-aminoethyl)amine HPHA - Hydroxypropylhydroxylamine OH OH
~\cH2NHcH2cH2NHcH2/~
wherein R is H or OH
These results show that the polyamines provide high percent transmittance which is indicative of inhibition of color formation.
Example 4 The procedure of example 3 was followed except small pieces of carbon steel were present. These results are shown in Table IV.
7 ~ ~
TABLE IV
Triethanolamine color development 4000 parts per million active at 190C
Argon Purged 1010 Carbon Steel 9 CRlM0 Carbon Steel %T %T %T
Treatment24 Hours 48 Hours 62 Hours None 3.0 3.5 0.0 DETA 23.5 40.0 1.0 TETA 24.0 36.0 1.0 TEPA 38.0 52.0 1.0 DETA = Diethylenetriamine TETA = Triethylenetetramine TEPA = Tetraethylenepentamine These results again show that the polyamines inhibited color formation in the ethanolamines.
While this invention has been described with respect to particular embodiments thereof, it is apparent that numerous other forms and modifications of this invention will be obvious to those skilled in the art.
METHOD FOR INHIBITING COLOR CONTAMINATION
IN ETHANOLAMINE COMPOUNDS
FIELD OF THE INVENTION
The present invention is directed to a method of inhibiting color formation and contamination in ethanolamine compounds. More specifically, the present invention is directed to a method of using amine compounds to inhibit the formation of oxygen containing compound impurities which cause color contamination in ethanolamine compounds.
BACKGROUND OF tHE INYENTION
Ethanolamine compounds, which include monoethanolamine, diethanolamine and triethanolamine, are produced commercially by reacting ethylene oxide, ammonia and water in a tubular reactor.
Oftentimes, the compounds generated by this method exhibit an undesirable color and color instability developed over a period of time. Nickel contained in the process system metallurgy is thought to catalyze dehydrogenation reactions of by-product ethylene glycol. It is thought that these reactions form oxygen containing carbonyl compounds such as aldehydes and ketones.
The aldehyde compounds can undergo the aldol-condensation reactions in the process system environment. Nickel may also catalyze the direct decomposition of the ethanolamine compounds, further forming carbonyl compounds.
2~71~
One theory postulates that these condensation polymer-ization contaminants thus formed can cause color contamination problems in the finished ethanolamine product.
Avoidance of color contamination increases the value of the ethanolamine compound to the producer and minimizes the off-specification product manufactured.
SUMMARY OF THE INVENTION
The present invention provides for a method for inhibiting color formation in ethanolamine compounds comprising adding to said ethanolamine compounds an effective amount for the purpose of an amine compound of the formula R"
, N - (CH2)x - R' R
wherein R is H or OH; R' is - NH (CH2CH2NH)yH
where y is an integer from about 0 to about 20, r\ r~ ~
--N NH, --N N - (CH2)2NH2. --N\__/N - (CH2)3 NH2 OH
CH3 - CH, - , --N((CH2 CH2)NH2)2, OH
- NH(cH2cH2NH)zcH2 ~ where z is 0,1,2,3,4, R''' 2~7~
OH
R" is H or (CH2)X-R' or -CH2 ~ and R''' OH OH
R''' is ~ CH2NHcH2cH2NHcH2 ~ O J
R R
and x is about 1 to about 3.
While effective in all ethanolamine compounds, the method of the present invention is particularly effective at inhibiting color formation in monoethanolamine, diethanolamine and triethanolamine.
The present method entails ensuring that the amine compounds are present in the ethanolamine reactor effluent.
DESCRIPTION OF THE RELATED ART
United States Patent 4,952,301, Awbrey, August 1990, dis-closes a method of inhibiting the formation of polymeric fouling deposits formed during the caustic washing of hydrocarbons. This method employs the use of an ethylenediamine compound.
2~7~8 United States Patent 3,819,710, Jordan, June 1974, discloses a process for improving the color and color stability of ethanolamine compounds. This process comprises hydrogenation of crude mono - , di and triethanolamines using selected catalysts at specific temperatures and pressures.
United States Patent 4,673,762, Paslean et al., June 1987, discloses a method for decolorizing ethanolamine compounds. This method employs adding to the ethanolamine compound an alkyleneoxide such as ethylene oxide.
Japanese Patent Publication No. 1977 - [Showa 52]-28,770 discloses a method of decoloring ethyleneamines and alkanolamines.
This method is accomplished by heat treatment of the amine compound in the presence of hydrogen and a catalyst. The catalyst can be selected from a nickel-type, cobalt-type or nickel-cobalt-mixed type hydrogenation catalyst.
European patent registration A1 0,004,015 discloses a process for the manufacture of colorless ethanolamines. This process entails carrying out the ethylene oxide, ammonium, water reaction in the presence of phosphorous acid or hypophosphorous acid or their compounds.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides for a method for inhibiting color formation in ethanolamine compounds comprising adding to said 2 ~ ~ 1 r7 ethanolamine compounds an effective amount for the purpose of an amine compound of the formula R"
, N - (CH2)x - R' R
wherein R is H or OH; R' is - NH (CH2CH2NH)yH
where y is an integer from about O to about 20, /~\ / \ ~
--N NH, --N N - (CH2)2NH2, --N\~_ /N - (CH2)3 NH2 OH
CH3 - CH, - , --N((CH2 CH2)NH2)2 OH
- NH(CH2CH2NH)zcH2 ~ where z is 0,1,2,3,4, R''' OH
R" is H or (CH2)X-R' or -CH2 ~ and R''' OH OH
R''' is ~ CH2NHCH2CH2NHcH2 R R
and x is about 1 to about 3.
2~ 7~ ~
Of these compounds, tetraethylenepentamine is preferred.
In addition, exemplary compounds include diethylenetriamine and triethylenetetramine. The tetraethylenepentamine is preferred as it possesses a higher boiling point than the other two compounds and thus can inhibit color formation at higher temperatures.
These amine compounds are also ashless compounds. This makes their use desirable as industry is moving away from ash containing compounds due to the clean-up costs involved.
These color inhibiting compounds can be added to the ethanolamine compounds as neat materials or in solution form.
The preferred method of addition is as an aqueous solution.
The treatment should be added to the ethanolamine in sufficient quantity to ensure there is enough of the amine compound present to react with all the undesirable carbonyl contaminants. Treatment dosages in the range of from about 1 part per million to about 10,000 parts per million parts of ethanolamine compound may be employed. Preferably, the amine compound is added in a range of about 5 parts per million to about 5000 parts per million parts of the ethanolamine compound to be treated.
The invention will be further illustrated by the following examples which are intended merely for purpose of illustration and are not to be regarded as limiting the scope of the invention or the manner in which it may be practiced.
2 0 ~
EXAMPLES
Examp~e 1 In a 17 ml test tube, 10.0 ml of triethanolamine was added. 40 ul of treatment (160 ul of 25% solution) was also - 5 added along with a piece of steel. The remaining 7 ml of air space was then purged with argon for 60 seconds and then the cap was securely fastened. The test tube was then placed in a sili-cone oil bath at the appropriate temperature for the specified time indicated in the table. The time in days represents how many days since the reaction was started. The yellow to brown colors were then compared visually. The results of this first test appear in Table I.
TABLE I
Triethanolamine color development 310 stainless steel 4,000 parts per million actives Days Since Reaction Temperature ofOrder of Color Started Bath (C) (Darkest to Lightest) 5 144 HS > TETA > NP > Blank, Blank No SS
7 204 HS > Blank No SS > TETA, NP, Blank 8 204 Blank No SS > HS > Blank > NP > TETA
9 204 Blank No SS > HS > Blank > NP > TETA
HS = Hydroxylamine sulfate NP = Nonylphenol TETA = Triethylenetetramine Blank No SS - Blank run with no stainless steel present.
2a~7~
The results of this test indicate that triethylene-tetramine is more effective at inhibiting color formation than the blank runs over a greater length of time and temperature.
Example 2 The procedure of example 1 was followed here. These results are shown in Table II.
TABLE II
Triethanolamine color development 4000 parts per million active at 168C
Days Since Reaction Order of Color Started(Darkest to Liqhtest) With 310 SS Present 2 HS > TETA > EDA > Blank > NP > DETA = TEPA
4 HS > TETA > EDA > Blank > NP > DETA = TEPA
Without 310 SS Present 2 HS > EDA > NP > Blank = TETA = DETA = TEPA
4 HS > Blank > NP > EDA = TETA = DETA = TEPA
HS = Hydroxylamine Sulfate EDA = Ethylenediamine NP = Nonylphenol : TETA = Triethylenetetramine DETA = Diethylenetriamine TEPA = Tetraethylenepentamine 21~ 1 7~
The polyamines diethylenetriamine and tetraethylenepent-amine were always less colored than the blanks. The polyamines ethylenediamine and triethylenetetramine proved better than the blanks at longer heating periods with no steel present.
Example 3 The procedure of example 1 was followed. The tubes were then wiped clean and inserted into a Hach spectrophotometer set at 410nm and calibrated with an unheated, untreated triethanolamine sample. The results are presented in Table III as % transmittance (%T)-TABLE III
Triethanolamine Color Development 4000 parts per million active at 190C
No 310 SS present %T %T %T %T
Treatment 24 Hours 48 Hours 62 Hours 24 Hours ---------Argon Purged----------- Air Purged None 3.5,3.0 1.0,2.5 0.7 0.2 EDA - 64.0 - 4.0 DETA 73.0 63.0 - 7.5 2~ 7~8 TABLE III (Cont'd) %T %T %T %T
Treatment 24 Hours 48 Hours 62 Hours 24 Hours ---------Argon Purged----------- Air Purged .
TEPA 58.5 - 11.0 AEP 44.0 BISAPP 66.5 TREN 27.0 HPHA 25.0 MD 35.0 EDA = Ethylenediamine DETA = Diethylenetriamine TETA = Triethylenetetramine TEPA = Tetraethylenepentamine AEP = N-(2-aminoethyl)piperazine BISAPP = N,N'-bis(3-aminopropyl)piperazine TREN = Tris(2-aminoethyl)amine HPHA - Hydroxypropylhydroxylamine OH OH
~\cH2NHcH2cH2NHcH2/~
wherein R is H or OH
These results show that the polyamines provide high percent transmittance which is indicative of inhibition of color formation.
Example 4 The procedure of example 3 was followed except small pieces of carbon steel were present. These results are shown in Table IV.
7 ~ ~
TABLE IV
Triethanolamine color development 4000 parts per million active at 190C
Argon Purged 1010 Carbon Steel 9 CRlM0 Carbon Steel %T %T %T
Treatment24 Hours 48 Hours 62 Hours None 3.0 3.5 0.0 DETA 23.5 40.0 1.0 TETA 24.0 36.0 1.0 TEPA 38.0 52.0 1.0 DETA = Diethylenetriamine TETA = Triethylenetetramine TEPA = Tetraethylenepentamine These results again show that the polyamines inhibited color formation in the ethanolamines.
While this invention has been described with respect to particular embodiments thereof, it is apparent that numerous other forms and modifications of this invention will be obvious to those skilled in the art.
Claims (16)
1. A method for inhibiting color formation in ethanolamine compounds comprising adding to said ethanolamine compound an effective amount for the purpose of an amine compound of the formula wherein R is H or OH; R' is - NH (CH2CH2NH)yH
where y is an integer from about 0 to about 20, , , , , --N(((CH2 CH2)NH2)2, where z is 0,1,2,3,4, R" is H or (CH2)x-R' or and R''' is and x is about 1 to about 3.
where y is an integer from about 0 to about 20, , , , , --N(((CH2 CH2)NH2)2, where z is 0,1,2,3,4, R" is H or (CH2)x-R' or and R''' is and x is about 1 to about 3.
2. The method as claimed in claim 1 wherein said amine compound is diethylenetriamine.
3. The method as claimed in claim 1 wherein said amine compound is triethylenetetramine.
4. The method as claimed in claim 1 wherein said amine compound is tetraethylenepentamine.
5. The method as claimed in claim 1 wherein said amine compound is added to said ethanolamine compound from about 1 part per million to about 10,000 parts per million parts of said ethanolamine compound.
6. The method as claimed in claim 1 wherein said amine compound is added to said ethanolamine compound from about 5 parts per million to about 5000 parts per million parts of said ethanolamine compound.
7. The method as claimed in claim 1 wherein said ethanolamine compound is monoethanolamine.
8. The method as claimed in claim 1 wherein said ethanolamine compound is diethanolamine.
9. The method as claimed in claim 1 wherein said ethanolamine compound is triethanolamine.
10. A method for inhibiting color formation in ethanolamine compounds comprising adding to said ethanolamine compound an effective amount for the purpose of at least two amine compounds of the formula wherein R is H or OH; R' is - NH (CH2CH2NH)yH
where y is an integer from about 0 to about 20, , , , --N((CH2 CH2)NH2)2, where z is 0,1,2,3,4, R" is H or (CH2)x-R' or and R''' is and x is about 1 to about 3.
where y is an integer from about 0 to about 20, , , , --N((CH2 CH2)NH2)2, where z is 0,1,2,3,4, R" is H or (CH2)x-R' or and R''' is and x is about 1 to about 3.
11. The method as claimed in claim 10 wherein said mixture consists essentially of diethylenetriamine, triethylene-tetramine and tetraethylenepentamine.
12. The method as claimed in claim 10 wherein said mixture is added to said ethanolamine compound from about 1 part per million to about 10,000 parts per million parts of said ethanolamine.
13. The method as claimed in claim 10 wherein said mixture is added to said ethanolamine compound from about 5 parts per million to about 5000 parts per million parts of said ethanolamine compound.
14. The method as claimed in claim 10 wherein said ethanolamine compound is monoethanolamine.
15. The method as claimed in claim 10 wherein said ethanolamine compound is diethanolamine.
16. The method as claimed in claim 10 wherein said ethanolamine compound is triethanolamine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70394691A | 1991-05-22 | 1991-05-22 | |
| US07/703,946 | 1991-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2061718A1 true CA2061718A1 (en) | 1992-11-23 |
Family
ID=24827422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2061718 Abandoned CA2061718A1 (en) | 1991-05-22 | 1992-02-24 | Method for inhibiting color contamination in ethanolamine compounds |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2061718A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001053250A1 (en) * | 2000-01-24 | 2001-07-26 | Bp Chemicals Limited | Process for manufacturing triethanolamine and product obtained |
| IT201700057247A1 (en) * | 2017-05-26 | 2018-11-26 | Valagro Spa | KELANIC AGENTS FOR THE TREATMENT OF NUTRITIONAL DISORDERS OF PLANTS |
| US10662144B2 (en) | 2015-12-11 | 2020-05-26 | Sabic Global Technologies B.V. | Method of reducing color in alkanolamine compositions and compositions produced thereby |
| US11203568B2 (en) | 2015-12-29 | 2021-12-21 | Sabic Global Technologies B.V. | Methods of reducing color in alkanolamine compositions and compositions produced thereby |
-
1992
- 1992-02-24 CA CA 2061718 patent/CA2061718A1/en not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001053250A1 (en) * | 2000-01-24 | 2001-07-26 | Bp Chemicals Limited | Process for manufacturing triethanolamine and product obtained |
| FR2804109A1 (en) * | 2000-01-24 | 2001-07-27 | Bp Chemicals Snc | Continuous preparation of triethanolamine, useful in pharmacy, involves reacting ethylene oxide with ammonia to give mixture of mono-, di- and tri-ethanolamine; and separating unreacted ammonia and triethanolamine from mixture |
| US10662144B2 (en) | 2015-12-11 | 2020-05-26 | Sabic Global Technologies B.V. | Method of reducing color in alkanolamine compositions and compositions produced thereby |
| US11746080B2 (en) | 2015-12-11 | 2023-09-05 | Sabic Global Technologies B.V. | Methods of reducing color in alkanolamine compositions and compositions produced thereby |
| US11203568B2 (en) | 2015-12-29 | 2021-12-21 | Sabic Global Technologies B.V. | Methods of reducing color in alkanolamine compositions and compositions produced thereby |
| US11702382B2 (en) | 2015-12-29 | 2023-07-18 | Sabic Global Technologies B.V. | Methods of reducing color in alkanolamine compositions and compositions produced thereby |
| IT201700057247A1 (en) * | 2017-05-26 | 2018-11-26 | Valagro Spa | KELANIC AGENTS FOR THE TREATMENT OF NUTRITIONAL DISORDERS OF PLANTS |
| EP3406590A1 (en) * | 2017-05-26 | 2018-11-28 | Valagro S.p.A. | Chelating agents for treating nutritional disorders of plants |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2068179C (en) | Amine derivatives as corrosion inhibitors | |
| US4316841A (en) | Reforming linear polyamines | |
| US4463193A (en) | Production of noncyclic polyalkylene polyamines | |
| US4324917A (en) | Preparation of polyalkylene polyamines | |
| US4096085A (en) | Gas scrubbing system | |
| EP0138050A2 (en) | Polyalkylene polyamines from alkanolamine and ammonia or amines using group IIIB metal acid phosphate catalysts | |
| CA1210022A (en) | Use of quaternized polyamidoamines as demulsifiers | |
| US4766247A (en) | Color reduction of polyamines by mild catalytic hydrogenation | |
| JP4772976B2 (en) | Process for the preparation of alkanolamines with improved color quality | |
| US4503253A (en) | Production of noncyclic polyalkyene polyamines | |
| JPS60169448A (en) | Manufacture of mainly non-cyclic polyalkylene polyamine | |
| CA2061718A1 (en) | Method for inhibiting color contamination in ethanolamine compounds | |
| CA1105947A (en) | Catalyst pellet stabilization in the preparation of polyamines from polynitriles | |
| SE9500444D0 (en) | Method for producing aminoethylethanolamine and / or hydroxyethyl piperazine | |
| US2318730A (en) | Process of making alkylene polyamines | |
| US5415785A (en) | Method for removing a cyanide contaminant from refinery waste water streams | |
| US4440666A (en) | Method of making corrosion inhibiting polyamine amides, the amides, and use therefor | |
| CA2354773C (en) | Cyanoethylation of cycloaliphatic vicinal primary diamines | |
| US7335794B2 (en) | Polythiaether compounds and their use as corrosion inhibitors | |
| US4497702A (en) | Corrosion inhibition | |
| RU2118649C1 (en) | Method of removing hydrogen sulfide from crude oil and gas condensate | |
| US5387393A (en) | Prevention of cracking and blistering of refinery steels by cyanide scavenging in petroleum refining processes | |
| ES2223341T5 (en) | PROCESS TO PRODUCE A COMPOUND OF PRIMARY AMINA. | |
| JPH0782222A (en) | Decoloration of polyethylene polyamine using ruthenium | |
| US6074532A (en) | Adjunct for removal of aldehydes from chemical manufacturing production streams during distillative purification |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |