European winters are great for low boiling point distillations! I just made bromine today and I lost barely any by evaporation because it is about 5C. Thankfully it's not too cold either so the distillation water doesn't freeze.
You have to be congratulated on pointing out as many dangers as possible. I find it highly refreshing to see such responsibility in videos like these.... Respect ✋
Great project, I might have to try it if I ever get my hands on formic acid! This actually reminded me a lot of isopropyl chloride (something I made in my last video): both have boiling points below body temperature, smell "fruity", and are extremely flammable...the main difference being isopropyl chloride is more toxic, distills off with a lot of dissolved HCl, and the synthesis took the whole day, lol. Anyway, can't wait for the next video!
@@THYZOID Thanks man, alkyl halides are pretty fun to make, but the neutralization steps are a bit of a pain and the compounds tend to be classified as "possible mutagens", so they sadly aren't as handleable as some other esters like methyl formate.
I wonder how hard it is to make isopropyl formate? Apparently it's found naturally in Caffea arabica beans and is used as both a flavouring and fragrance agent.
When I made my own methyl formate a while ago, I discovered that formic acid is acidic enough that the reaction didn't need any sulfuric acid catalyst, and all I added was a bit of calcium chloride granules as boiling chips/drying agent. The final yield was a bit lower, but I think that was mostly because I merely did a simple distillation and it was summer, which means that I lost some of the product due to evaporation.
Calcium chloride is classic dehydrating agent for esterifications with formic acid. I used it for my preparation of methyl formate, but yield wasn't good, about 65%. Sulfuric acid isn't necessary at all. The weirdest thing in methyl formate distillation is that the setup stays cold all the time in relation to the hands.
Methyl formate was used as a low pressure refrigerant (R-611), the most common application being in GE CA Monitor Top refrigerators as an attempt at getting away from using highly toxic sulphur dioxide. The only problem is that it hydrolyses to methanol and formic acid, which further decomposes to produce more methanol and CO gas which becomes trapped in the system, requiring regular purges to eliminate this non-condensable gas. Dichloromethane (R-30) has been found to be a suitable substitute in this application and was also used in early centrifugal chillers and Grunow household refrigerators.
Chemdraw is the standard drawing program in chemistry. Everything else is questionable. While its not free there are many ways to get a free version of it.
For drawing reactions I used some online tools, they are a bit cumbersome though (all of them) Forgot exact ones I used, but it tookme like 30 minutes to find something I can export png's at custom resolution
Should add a dry-ice acetone cold trap to help to collect the low boiling point methyl formate; also the collector should be cooled by the dry-ice acetone cold bath too.
@@THYZOID Your answer remind me the old days in Univ. of Minnesota, an old joke between lab geeks. What's the temp. today? It's -40 C today. Great, let's open the window to do Birch reduction (e.g. sodium in anhydrous liquid ammonium, bp -33 C).
@@THYZOID ChemDraw isn't the best program for mechanism drawing because you can't pin arrows somewhere. It works only if you have good eye and hard hand. I advice using the second one from Pen Tools, it looks better than usual arrow. I can help you with it btw. Just send me a gmail letter
I hate having to wait for a long time with everything. That’s why I love using low boiling solvents. The lower the boiling point the faster it starts to boil. It’ll become harder to condense but the time saved is worth it. In comparison to dichloromethane it is less toxic and its vapors are less explosive than those of diethyl ether .
@@THYZOID Distillation time depends on solvent's molar mass and boiling enthalpy specific heat of boiling. It isn't related to temperature. Low-boiling solvents are nasty to work due to their high vapor pressure (extraction funnels, distillation, storage). I prefer solvents with bp between chloroform and toluene inclusively.
@@THYZOID Für LaTeX gibt es mehrere Pakete um chemische Formeln und Strukturdiagramme in professioneller Art und Weise darzustellen: Z.B. chemfig, ochem, streeTeX, XyMTeX, PPCHTeX von ConTeXt und andere. Das beim Paket chemtex (Structural chemistry) beiliegende "Typesetting Chemical Equations using LATEX"-Dokument geht im Detail darauf ein, wie die Darstellung von chemischen Formeln und Strukturdiagrammen im Detail funktioniert. Du hast hier also eher die Qual der Wahl:) Danke für eure tollen Videos!
@@THYZOID Die "Can you make chemical structure diagrams in LaTeX?"-Frage bei stackexchange kann hier erste Anlaufstelle sein und einen groben Überblick gewähren. Ich bitte um Verzeihung für die deutschsprachige Antwort. Da mir aber beim Lesen von diesem Kommentarfaden, inklusive der sprichwörtlichen Sparsamkeit (Effektivität? **augenroll** ) des Englischen die hier anscheinend ihre Blüten ins Absurde getrieben hat kurzzeitig der Würgereiz einsetzte, bevorzuge ich aus reinem Trotz und Sturheit hier die Deutsche Sprache:P Hehehehe
@@THYZOID The idea is to do a haloform reaction between sodium hypochlorite, sodium hydroxide and ethanol which gives sodium chloride, sodium formate and water. It´s optional but you can separate the sodium formate from the sodium chloride using ethanol as the solvent. The sodium formate can then be turned into formic acid, which is collected by distillation.
Bei dieser Synthese habe ich den ganzen Rest einfach in einen Kanister geschüttet den ich irgendwann professionell entsorgen lasse. Alles wurde kurz mit Wasser ausgespült (kleine Menge dem Kanister hinzugegeben) bevor einmal alles mit Spülmittel und Wasser und anschließend einmal mit destilliertem Wasser ausgespült wurde. Cleanup Videos mache ich ausschließlich bei problematischen Chemikalien allerdings kommt demnächst ein Video das auf Glasgerätreinigung ausgelegt ist.
European winters are great for low boiling point distillations! I just made bromine today and I lost barely any by evaporation because it is about 5C. Thankfully it's not too cold either so the distillation water doesn't freeze.
You have to be congratulated on pointing out as many dangers as possible. I find it highly refreshing to see such responsibility in videos like these.... Respect ✋
ChemDraw! It's great for drawing compounds and mechanisms. This is a cool project. Thanks for sharing.
"killing quickly and diligently" gave me a chuckle tbh.
Great project, I might have to try it if I ever get my hands on formic acid! This actually reminded me a lot of isopropyl chloride (something I made in my last video): both have boiling points below body temperature, smell "fruity", and are extremely flammable...the main difference being isopropyl chloride is more toxic, distills off with a lot of dissolved HCl, and the synthesis took the whole day, lol. Anyway, can't wait for the next video!
Thanks mate! I’ll have to check out your video on isopropyl chloride immediately! I might make isopropyl bromide someday.
@@THYZOID Thanks man, alkyl halides are pretty fun to make, but the neutralization steps are a bit of a pain and the compounds tend to be classified as "possible mutagens", so they sadly aren't as handleable as some other esters like methyl formate.
I wonder how hard it is to make isopropyl formate? Apparently it's found naturally in Caffea arabica beans and is used as both a flavouring and fragrance agent.
When I made my own methyl formate a while ago, I discovered that formic acid is acidic enough that the reaction didn't need any sulfuric acid catalyst, and all I added was a bit of calcium chloride granules as boiling chips/drying agent. The final yield was a bit lower, but I think that was mostly because I merely did a simple distillation and it was summer, which means that I lost some of the product due to evaporation.
Calcium chloride is classic dehydrating agent for esterifications with formic acid. I used it for my preparation of methyl formate, but yield wasn't good, about 65%. Sulfuric acid isn't necessary at all.
The weirdest thing in methyl formate distillation is that the setup stays cold all the time in relation to the hands.
I also found that interesting! A cold apparatus you can just touch while distilling.
Methyl formate was used as a low pressure refrigerant (R-611), the most common application being in GE CA Monitor Top refrigerators as an attempt at getting away from using highly toxic sulphur dioxide. The only problem is that it hydrolyses to methanol and formic acid, which further decomposes to produce more methanol and CO gas which becomes trapped in the system, requiring regular purges to eliminate this non-condensable gas. Dichloromethane (R-30) has been found to be a suitable substitute in this application and was also used in early centrifugal chillers and Grunow household refrigerators.
Thanks for the amazing content! Do you think in the future, making some nice smelling compounds, with some more synthesis steps?
I’m planning to make a nice smelling ester of phenylacetic acid and also other compounds too. Any specific recommendations?
Chemdraw is the standard drawing program in chemistry. Everything else is questionable. While its not free there are many ways to get a free version of it.
For drawing reactions I used some online tools, they are a bit cumbersome though (all of them) Forgot exact ones I used, but it tookme like 30 minutes to find something I can export png's at custom resolution
You could use Marvin Sketch for drawing the reaction mechanism.
Understated enthusiasm; I like it.
Very efficient reaction.
Should add a dry-ice acetone cold trap to help to collect the low boiling point methyl formate; also the collector should be cooled by the dry-ice acetone cold bath too.
It was -7*C outside. This should have condensed most of the product anyways.
@@THYZOID Your answer remind me the old days in Univ. of Minnesota, an old joke between lab geeks.
What's the temp. today? It's -40 C today. Great, let's open the window to do Birch reduction (e.g. sodium in anhydrous liquid ammonium, bp -33 C).
where do you got those chemicals from
Acdlabs is free for drawing, but I have chemdraw and could whip up some mechanisms if you want.
Thanks for the offer and the apps! Is it easy to draw mechanisms via chemdraw?
@@THYZOID yes, chemdraw is extremely easy to use. ACDlabs takes more getting used to, but as i said, is free, unlike chemdraw.
@@THYZOID ChemDraw isn't the best program for mechanism drawing because you can't pin arrows somewhere. It works only if you have good eye and hard hand. I advice using the second one from Pen Tools, it looks better than usual arrow. I can help you with it btw. Just send me a gmail letter
@@dimaminiailo3723 you can align things and that's usually plenty to draw a good mechanism.
Out of context but don't you think t your tabke is slightly slanted toward right ? Mine too 😂!
maybe
Hi is this the synthesis of N methyl formamide?
read the title of this video....
Chemdraw is amazing, gotta have a license though
Darf ich fragen wo genau du herkommst?
Hessen
Ahh, hallo Nachbar
Nähe Darmstadt um etwas spezifischer zu sein. Du?
Baden-Württemberg im Südwesten in der nähe von Freiburg
Ich meinte wir sind Bundesland-Nachbarn
Avogadro 2 is a very good and free drawing software and it is capable to work with plug-ins.
Wo bekommt man in DE Methanol her? Irgendwie will das keiner versenden weil giftig.
Ich kenne ein Geschäft wo ich es kaufen und abholen kann.
@@THYZOID So ein Laden fehlt mir.
One question, why are need it? For why?
I hate having to wait for a long time with everything. That’s why I love using low boiling solvents. The lower the boiling point the faster it starts to boil. It’ll become harder to condense but the time saved is worth it. In comparison to dichloromethane it is less toxic and its vapors are less explosive than those of diethyl ether .
@@THYZOID Distillation time depends on solvent's molar mass and boiling enthalpy specific heat of boiling. It isn't related to temperature.
Low-boiling solvents are nasty to work due to their high vapor pressure (extraction funnels, distillation, storage). I prefer solvents with bp between chloroform and toluene inclusively.
How about trimethylortho formate?
It is a little harder to make and requires different chemicals.
Chemdraw?
What does methyl formate smell like?
i don´t know how to describe it. theres nothing i know similar to it
@THYZOID I suppose it smells a bit like ethyl acetate which is structurally similar to methyl formate?
@@vxbrxnt no. totally different smell
Latex for drawing?
?
@@THYZOID drawing mechanism
You mean which program?
@@THYZOID Für LaTeX gibt es mehrere Pakete um chemische Formeln und Strukturdiagramme in professioneller Art und Weise darzustellen: Z.B. chemfig, ochem, streeTeX, XyMTeX, PPCHTeX von ConTeXt und andere. Das beim Paket chemtex (Structural chemistry) beiliegende "Typesetting Chemical Equations using LATEX"-Dokument geht im Detail darauf ein, wie die Darstellung von chemischen Formeln und Strukturdiagrammen im Detail funktioniert. Du hast hier also eher die Qual der Wahl:) Danke für eure tollen Videos!
@@THYZOID Die "Can you make chemical structure diagrams in LaTeX?"-Frage bei stackexchange kann hier erste Anlaufstelle sein und einen groben Überblick gewähren.
Ich bitte um Verzeihung für die deutschsprachige Antwort. Da mir aber beim Lesen von diesem Kommentarfaden, inklusive der sprichwörtlichen Sparsamkeit (Effektivität? **augenroll** ) des Englischen die hier anscheinend ihre Blüten ins Absurde getrieben hat kurzzeitig der Würgereiz einsetzte, bevorzuge ich aus reinem Trotz und Sturheit hier die Deutsche Sprache:P Hehehehe
+THYZOID LABORATORIES Did you know it´s possible for you to make formic acid using sodium hypochlorite?
Haven’t even thought about making it before as I can buy it really cheaply. Thanks for mentioning! Just looked into the procedure out of curiosity.
@@THYZOID The idea is to do a haloform reaction between sodium hypochlorite, sodium hydroxide and ethanol which gives sodium chloride, sodium formate and water. It´s optional but you can separate the sodium formate from the sodium chloride using ethanol as the solvent. The sodium formate can then be turned into formic acid, which is collected by distillation.
@@chemicalmaster3267 Reference?
Anyone thinking: chlorinate the esther? No? Just me? Oh, well! Nice job!
Thought about it but besides not wanting to work with anything phosgene related I don’t know if it is legal.
@@THYZOID pretty sure it isn't (or it shouldn't be)
Chemdraw is great
Bitte zeig mal wie du am Ende alles säuberst
Bei dieser Synthese habe ich den ganzen Rest einfach in einen Kanister geschüttet den ich irgendwann professionell entsorgen lasse. Alles wurde kurz mit Wasser ausgespült (kleine Menge dem Kanister hinzugegeben) bevor einmal alles mit Spülmittel und Wasser und anschließend einmal mit destilliertem Wasser ausgespült wurde.
Cleanup Videos mache ich ausschließlich bei problematischen Chemikalien allerdings kommt demnächst ein Video das auf Glasgerätreinigung ausgelegt ist.
Do you prepare ethyl formate?
Yes but not this year.
👍👍sehr schönes Video
Isopropyl nitrite burns even better
And with an interesting flame color
Diphosgene
this is like ethyl acetate but smaller
You can see French is not being taught on the continent anymore outside the obviously co- Francophone countries.
But 'human body temperature' needs more research...
I know how to get this as a polyol, and it takes no sulphuric acid, and its easier.
polyol?
@@THYZOID methyl poly formate. it has more moles of formic acid in it, and its thick and viscous and has a higher boiling point.
😅
cool
I like German accent.
You got fever bcz normal body temperature is 37 degree Celsius.