Synthesis of 1-heptyl acetate (1-alkyl alkanoates) as hands-on experiments for school pupils
ID: 132019 | No.: 432 | Institut für Chemieinformation
School experiment from Year 5 onwardsCategory: Esters, fats, surfactants
Acid esterification is an equilibrium reaction in which the water formed by the reaction is absorbed by the hygroscopic sulphuric acid and is thus removed from the equilibrium. Image: Wikipedia
The pupils add approximately 2 mL of heptanol and three boiling chips to a test tube containing a mixture of 3 mL of concentrated acetic acid and 0.5 mL of concentrated sulphuric acid, using a pipette fitted with a Pileus ball. The test tube is then sealed with the stopper and rising tube and clamped into a test tube holder
. The hot-air blower is placed upright on the student experiment bench and switched on. The test tube is now held at an angle in the hot-air stream for short intervals of 10–20 s at a time, whilst being shaken gently. This procedure is repeated twice, after approximately 30 s each time.
Clean-up:
Once the test tube has cooled to room temperature, the reaction mixture is carefully poured into the beaker, which has been pre-filled with 20 mL of cold water. After one minute, the contents of the beaker can be poured back into the test tube. The resulting ester separates as a water-clear oily phase above the aqueous phase.
Notes:
The aqueous acid solution can be coloured by adding a drop of the indicator methyl orange. The phase boundary between the ester and the aqueous phase, which has been coloured red, is then easier to recognise. Alternatively, it is possible to neutralise the aqueous phase before separating the ester by adding magnesium oxide, causing the colour to change from red to yellow.
This method is suitable for the combinatorial synthesis of 1-alkyl alkanoates. The quantities must be adjusted in accordance with the molar masses of the starting materials.
|
Acid |
Name |
Ethanol |
1-propanol |
1-Butanol |
1-Pentanol |
1-hexanol |
1-Heptanol |
1-octanol |
|
Wikipedia |
||||||||
|
ZVG / ECHA |
||||||||
|
TheGoodScents |
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|
Wikipedia |
Hexyl propionate |
Heptyl propionate |
||||||
|
ZVG / ECHA |
||||||||
|
TheGoodScents |
||||||||
|
Wikipedia |
Heptyl butyrate |
|||||||
|
ZVG / ECHA |
||||||||
|
TheGoodScents |
Smell |
Test tube rack,
test tube (with rim),
50 mL beaker,
test tube holder,
rubber stopper with rising tube (l = approx. 20 cm),
pipette with Pileus ball
Pasteur pipette,
Hot-air blower (e.g. Steinel HL 1810 S),
boiling stones,
Disposable gloves,
Safety goggles
| Name | Formula | CAS no. | H-statements | P-statements | Pictograms |
|---|---|---|---|---|---|
| Essigsäure | CH₃COOH | 64-19-7 |
H226
– The liquid and vapour are flammable.
German original: Flüssigkeit und Dampf entzündbar.
H314
– Causes severe chemical burns to the skin and serious eye damage.
German original: Verursacht schwere Verätzungen der Haut und schwere Augenschäden. |
P210
– Keep away from heat, hot surfaces, sparks, open flames and other sources of ignition. No smoking.
German original: Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellen fernhalten. Nicht rauchen.
P280
– Wear protective gloves, protective clothing, eye protection and face protection.
German original: Schutzhandschuhe / Schutzkleidung / Augenschutz / Gesichtsschutz tragen.
P310
– Call the POISON INFORMATION CENTRE / a doctor ... immediately.
German original: Sofort GIFTINFORMATIONSZENTRUM / Arzt ... anrufen.
P301+P330+P331
– IF SWALLOWED: Rinse out the mouth. DO NOT induce vomiting.
German original: BEI VERSCHLUCKEN: Mund ausspülen. KEIN Erbrechen herbeiführen.
P303+P361+P353
– IF IN CONTACT WITH THE SKIN (or hair): Remove all contaminated clothing immediately. Wash skin with water or shower.
German original: BEI BERÜHRUNG MIT DER HAUT (oder dem Haar):Alle kontaminierten Kleidungsstücke sofort ausziehen. Haut mit Wasser abwaschen/duschen.
P305+P351+P338
– IF IN EYES: Rinse gently with water for several minutes. Remove any contact lenses if possible. Continue rinsing.
German original: BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Vorhandene Kontaktlinsennach Möglichkeit entfernen. Weiter spülen. |
GHS02, GHS05 |
| 1-Heptanol | C₇H₁₅OH | 111-70-6 |
H319
– Causes serious eye irritation.
German original: Verursacht schwere Augenreizung. |
P264
– After use … wash thoroughly.
German original: Nach Gebrauch ... gründlich waschen.
P280
– Wear protective gloves, protective clothing, eye protection and face protection.
German original: Schutzhandschuhe / Schutzkleidung / Augenschutz / Gesichtsschutz tragen.
P337+P313
– If eye irritation persists: Seek medical advice / seek medical attention.
German original: Bei anhaltender Augenreizung: Ärztlichen Rat einholen / ärztliche Hilfe hinzuziehen.
P305+P351+P338
– IF IN EYES: Rinse gently with water for several minutes. Remove any contact lenses if possible. Continue rinsing.
German original: BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Vorhandene Kontaktlinsennach Möglichkeit entfernen. Weiter spülen. |
GHS07 |
| Schwefelsäure 96% | H₂SO₄ | 7664-93-9 |
H290
– May be corrosive to metals.
German original: Kann gegenüber Metallen korrosiv sein.
H314
– Causes severe chemical burns to the skin and serious eye damage.
German original: Verursacht schwere Verätzungen der Haut und schwere Augenschäden. |
P234
– Store only in the original container.
German original: Nur im Originalbehälter aufbewahren.
P280
– Wear protective gloves / protective clothing / eye protection / face protection.
German original: Schutzhandschuhe / Schutzkleidung / Augenschutz / Gesichtsschutz tragen.
P363
– Wash contaminated clothing before wearing it again.
German original: Kontaminierte Kleidung vor erneutem Tragen waschen.
P303+P361+P353
– IF IN CONTACT WITH THE SKIN (or hair): Remove all contaminated clothing immediately. Wash the skin with water or take a shower.
German original: BEI BERÜHRUNG MIT DER HAUT (oder dem Haar):Alle kontaminierten Kleidungsstücke sofort ausziehen. Haut mit Wasser abwaschen/duschen.
P304+P340+P310
– IF INHALED: Take the person into fresh air and ensure they can breathe freely. Call a POISON INFORMATION CENTRE or a doctor immediately.
German original: BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen. Sofort GIFTINFORMATIONSZENTRUM oder Arzt anrufen.
P305+P351+P338
– IF THE PRODUCT COMES INTO CONTACT WITH THE EYES: Rinse gently with water for a few minutes. Remove any contact lenses if possible. Continue rinsing.
German original: BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Vorhandene Kontaktlinsennach Möglichkeit entfernen. Weiter spülen. |
GHS05 |
| Wasser, entionisiert | H₂O | 7732-18-5 | |||
| 1-Heptylacetat | C₉H₁₈O₂ | 112-06-1 |
H/P statements: machine translation, with the German original below (authoritative). Name, formula, CAS no. and pictograms are not translated.
-
Safety goggles must be worn.German originalEine Gestellschutzbrille ist zu tragen.
-
Disposable nitrile gloves are used as splash protection.German originalAls Spritzschutz dienen Nitril-Einmalhandschuhe.
The concentrated acetic acid and concentrated sulphuric acid are mixed under the fume cupboard. The laboratory is well ventilated (cross-ventilation). The prepared acid mixture is combined with the alcohol in the laboratory and heated there in a stream of hot air.
Die konz. Essigsäure und konz. Schwefelsäure werden unter dem Abzug gemischt. Der Fachraum wird gut gelüftet. (Querlüftung) Das vorgelegte Säuregemisch wird im Fachraum mit dem Alkohol versetzt und dort im Heißluftstrom erwärmt.
-
through skin contactGerman originaldurch Hautkontakt
-
through eye contactGerman originaldurch Augenkontakt
-
Fire hazardGerman originalBrandgefahr
-
Risk of explosionGerman originalExplosionsgefahr
-
Start-up firesFight small fires with a fire extinguisher. Pupils must keep a safe distance. If the fire cannot be extinguished immediately, leave the room straight away and alert the fire brigade and the school management. Fight fires involving people immediately using a hand-held hose or, if necessary, a fire extinguisher – every second counts!German originalEntstehungsbrände mit Feuerlöscher bekämpfen. Schülerinnen und Schüler halten sicheren Abstand. Können diese nicht sofort gelöscht werden, Raum unverzüglich verlassen und Feuerwehr sowie Schulleitung alarmieren. Personenbrände mit Handbrause oder ggf. Feuerlöscher unverzüglich bekämpfen, hier zählt jede Sekunde!
Note:
The ester syntheses can be carried out in a test tube fitted with a rising tube, or alternatively within 10 minutes in a water bath heated to approximately 80°C. However, this method eliminates the errors that can occur when heating with a hot-air gun – particularly those resulting from insufficient attention to the temperature or time specifications – thereby ensuring that the activity remains in the hands of the pupils.
Hinweis:
Die Estersynthesen können im Reagenzglas mit Steigrohr alternativ auch innerhalb von 10 Minuten in einem ca. 80°C warmen Wasserbad durchgeführt werden. Die Fehler, die beim Erwärmen mittels Heißluftgebläse insbesondere durch eine unzureichende Beachtung der Temperatur- bzw. der Zeitvorgaben gemacht werden können, werden dadurch aber zulasten der Schüleraktivität ausgeschlossen.
There are no known hazardous properties of the substances or other risks that would, in principle, preclude the experiment from being carried out by pupils or teachers. The list of substances in DGUV Information 213-098 at degintu.dguv.de has been taken into account.
In acid-catalysed esterification, certain equipment or processes cannot be replaced.
For information on the selection of substances, see “Safe Experimentation – Synthesis of nature-identical flavourings in chemistry lessons: ensuring safety through the use of substitute substances for the synthesis of flower, herb, vegetable and fruit flavourings”
Experiment protocol: Synthesis of 1-heptyl acetate (1:alkyl alkanoates) as a hands-on experiment for school pupils (2026) Klemeyer, H. DOI: 10.5281/zenodo.22832338
Horst Klemeyer (2008), The Experiment: Independent experiments on esters https://doi.org/10.1002/ckon.200890017
Horst Klemeyer (2021), The Experiment, Safe Experimentation – Synthesis of nature-identical flavourings in chemistry lessons. The substitute testing for the synthesis of floral, herbal, vegetable and fruit flavourings https://doi.org/10.1002/ckon.202000034