DE2455150C3 - N-formyl-iminodiacetic acid dimethyl ester, process for its preparation and its use for the extraction of aromatic hydrocarbons - Google Patents
N-formyl-iminodiacetic acid dimethyl ester, process for its preparation and its use for the extraction of aromatic hydrocarbonsInfo
- Publication number
- DE2455150C3 DE2455150C3 DE19742455150 DE2455150A DE2455150C3 DE 2455150 C3 DE2455150 C3 DE 2455150C3 DE 19742455150 DE19742455150 DE 19742455150 DE 2455150 A DE2455150 A DE 2455150A DE 2455150 C3 DE2455150 C3 DE 2455150C3
- Authority
- DE
- Germany
- Prior art keywords
- formyl
- iminodiacetic acid
- dimethyl ester
- acid dimethyl
- extraction
- 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
- -1 N-formyl-iminodiacetic acid dimethyl ester Chemical compound 0.000 title claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 4
- 238000000605 extraction Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- HFFLGKNGCAIQMO-UHFFFAOYSA-N Chloral Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- VNYJDSJLCWDYJK-UHFFFAOYSA-N methyl 2-[(2-methoxy-2-oxoethyl)amino]acetate Chemical compound COC(=O)CNCC(=O)OC VNYJDSJLCWDYJK-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical group 0.000 claims 2
- 150000001993 dienes Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 230000036698 Distribution coefficient Effects 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N Cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- TVSPOLBJUVJVCV-UHFFFAOYSA-N benzene;heptane Chemical compound C1=CC=CC=C1.CCCCCCC TVSPOLBJUVJVCV-UHFFFAOYSA-N 0.000 description 1
- LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 1
- QTCOXFCSKPJFCQ-UHFFFAOYSA-N hexane;1-methylpyrrolidin-2-one Chemical compound CCCCCC.CN1CCCC1=O QTCOXFCSKPJFCQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
CH2COOCH3 CH 2 COOCH 3
HNHN
+ Cl3CCHO + Cl 3 CCHO
CH2COOCH3
HCH 2 COOCH 3
H
O=C-O = C-
CH2-COOCH3 CH 2 -COOCH 3
+ CHCl1 + CHCl 1
CH2-COOCH3 CH 2 -COOCH 3
Die Formylierung wird erfindungsgemäß bei Atmosphärendruck und bei einer Temperatur durchgeführt, die anfänglich während mindestens einer Stunde bei oder unter O0C und anschließend während mindestens 2 Stunden bei Raumtemperatur gehalten wird.According to the invention, the formylation is carried out at atmospheric pressure and at a temperature which is initially kept at or below 0 ° C. for at least one hour and then at room temperature for at least 2 hours.
Das folgende Beispiel soll die Erfindung näher erläutern.The following example is intended to explain the invention in more detail.
Man löst 10 g Iminodiessigsäuredimethylester in 50 cm3 wasserfreiem Toluol. In den in ein Wasser/ Eis-Bad getauchten Reaktionskolben gibt man langsam 6 cm3 frisch über Schwefelsäure destilliertes Chloral. Dann rührt man das Reaktionsgemisch eine Stunde bei 0°C und 2 Stunden bei Raumtemperatur. Durch Destillation trennt man das Lösungsmittel ab und destilliert dann den öligen Rückstand im Vakuum. Ausbeute: 10 g (87%). Siedepunkt: 152°C/2,5 mm Hg η 1° 1,4639.10 g of dimethyl iminodiacetate are dissolved in 50 cm 3 of anhydrous toluene. 6 cm 3 of chloral freshly distilled over sulfuric acid are slowly added to the reaction flask immersed in a water / ice bath. The reaction mixture is then stirred for one hour at 0 ° C. and for 2 hours at room temperature. The solvent is separated off by distillation and the oily residue is then distilled in vacuo. Yield: 10 g (87%). Boiling point: 152 ° C / 2.5 mm Hg η 1 ° 1.4639.
Die mit N-Formyl-iminodiessigsäuredimethylester(in nachstehender Tabelle als A bezeichnet) bei der Extraktion aromatischer Kohlenwasserstoffe erhaltenen Ergebnisse sind aus dem Vergleich der Trennfaktoren für verschiedene Kohlenwasserstoffgemische bei verschiedenen Temperaturen ersichtlich:The with N-formyl-iminodiacetic acid dimethyl ester (designated in the table below as A) in the Extraction of aromatic hydrocarbons results obtained from the comparison of the separation factors visible for different hydrocarbon mixtures at different temperatures:
gemischHydrocarbon
mixture
raturTempe
rature
faktor
Sf Separating
factor
Sf
Benzol/HexanBenzene / hexane
Benzene / hexane
morpholin
AN-formyl
morpholine
A.
100°C100 ° C
100 ° C
2014th
20th
Benzol/n-HeptanToluene / n-heptane
Benzene / n-heptane
morpholin
AN-formyl
morpholine
A.
100°C100 ° C
100 ° C
16,9012.50
16.90
Benzol/HexanBenzene / hexane
Benzene / hexane
pyrrolidon
AN-methyl
pyrrolidone
A.
50° C50 ° C
50 ° C
23,116
23.1
Unter dem »Trennfaktor sf« für ein Kohlenwasser- für diesen Kohlenwasserstoff ein. Unter dem VerhältnisUnder the "separation factor sf" for a hydrocarbon - for this hydrocarbon. Below the ratio
stoffpaar ist das Verhältnis der Verteilungskoeffizienten von V1 : Xs versteht man den Verteilungskoeffizientensubstance pair is the ratio of the distribution coefficients of V 1 : Xs one understands the distribution coefficient
von jedem Kohlenwasserstoff in Anwesenheit eines D, für diesen Kohlenwasserstoff in dem bestimmtenof any hydrocarbon in the presence of a D, for that hydrocarbon in the particular one
bestimmten Lösungsmittels zu verstehen. Stellt bei- Lösungsmittel. Für den zweiten Kohlenwasserstoff des spielsweise Vi die Konzentration eines Kohlenwasser- 5 Kohlenwasserstoffpaares ergibt sich der Verteilungsko-to understand a specific solvent. Provides a solvent. For the second hydrocarbon des for example Vi is the concentration of a hydrocarbon pair, the distribution coefficient
stoffs in einem Kohlenwasserstoffgemisch dar, so stellt effizient D2. Das Verhältnis von D, : D2 soll densubstance in a hydrocarbon mixture, D 2 efficiently represents. The ratio of D,: D 2 should be the
sich im Gleichgewicht mit einem bestimmten Lösungs- »Trennfaktor sf«darstellen,
mittel in der Lösungsmittelphase die Konzentration X1 present themselves in equilibrium with a certain solution »separation factor sf« ,
medium in the solvent phase is the concentration X 1
Claims (3)
Siedepunkt: 152°C/2,5 mm Hg.
Brechungsindex: π 2S 1,4639.
Kinematische Viskosität bei 50°C: 37,65 cSt. Spezifisches Gewicht bei 5O0C: 1,2213 g/cm3. Bruttoformel: C7H11NO5.Melting point: 34 to 35 ° C.
Boiling point: 152 ° C / 2.5 mm Hg.
Refractive index: π 2 S 1.4639.
Kinematic viscosity at 50 ° C: 37.65 cSt. Specific weight at 5O 0 C: 1.2213 g / cm 3. Gross formula: C 7 H11NO 5 .
Ben: C 44,42, H 5,68, N 7,41%;
gef.: C 44,78, H 6,01, N 8,77%.Elemental analysis:
Ben: C 44.42, H 5.68, N 7.41%;
Found: C 44.78, H 6.01, N 8.77%.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3149973 | 1973-11-21 | ||
| IT3149973A IT1006639B (en) | 1973-11-21 | 1973-11-21 | PROCEDURE FOR THE PREPARATION OF N N BIS ACETOMETIL FORMAMIDE |
| BE151971A BE823906A (en) | 1973-11-21 | 1974-12-27 | PROCESS FOR PREPARING N, N'BIS ACETOMETHYLFORMAMIDE |
| BE823906 | 1974-12-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2455150A1 DE2455150A1 (en) | 1975-05-22 |
| DE2455150B2 DE2455150B2 (en) | 1977-05-12 |
| DE2455150C3 true DE2455150C3 (en) | 1977-12-29 |
Family
ID=
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