Below is Zac and my working document, planning and researching synthesizing cyanoacrylates to make superglue. The Google Doc link is on my main page, but it is here for easier access. I will update this with work when I journal (every week).

Last updated: March 20, 2025

Proposed timeline to present to Megan and Tim:

1. Write proposal - two weeks

2. Send proposal to Megan and Tim for revision

3. Time to review proposal before meeting - 1-2 weeks

4. Second meeting to discuss the proposal and any changes needed

5. Possibly repeat if parts of the proposal need to be changed

6. Order materials - unknown how long it will take to arrive

7. Possible practice methods (vacuum distillation if needed)

8. Begin cyanoacrylate synthesis (work will mostly be conducted during lunch and before and after school)

Things to be included in the proposal:

• Lab question and rough abstract

• Detailed procedure (including sources for step)

This means we will find a procedure to follow and then build our proposed procedure

• Make hypotheses

• Similar to mini-labs in class 

• Materials list (purity, price, and where to buy)

• Chemical safety information (summary of the dangers of every needed chemical with attached safety data sheets from credible sources)

• Procedure safety information (safe practices and methods we will take to prevent accidents and stay safe)

• The extension questions will be for us to look into the different aspects of organic chemistry we are working with 

The questions we are ultimately trying to answer: 

How can we adjust a procedure in the organic chemistry industry so that we can do it in high school?

What can be added to our synthesized α-cyanoacrylate to make it a better glue, and/or, depending on additives, how can it compete with other glues on the market?

Materials (just name from patent CN105541664A example 2) (planning to do ⅕ of these measurements): 

• 1452 g ethyl cyanoacetate

• 3g piperidine salt of methanosulfonate

• 1664 g diethoxymethane

• 75 mg (0.075 g) methanesulfonic acid

• 0.723 g hydroquinone

Equipment (from the same procedure):

• 4 necked flask (1 liter maybe? Translation is being iffy)

• Pipettes or buret (diethoxymethane needs to be added dropwise not sure which is best)

• Vacuum distillation set up (1.5 mbar / 200°C needed)

• General stirring and heating set up (stir bar affected by chemicals?)

Glassware and Equipment (Updated but must be rated for vacuum and we need extras):

• 1 four neck flask

• 4 roundbottom flasks (1 neck)

• Addition funnel (400 - 500 ml)

• Temp probe (tim has but we need to make sure we can attach it)

• Claisen adapter

• Short path vacuum distillation apparatus

• Tubing to run the vacuum and water

• 2 stoppers

SAFETY:

• Always where full body safety gear (flame-resistant lab coat, gloves, goggles/face shield etc.)

• Have fire extinguisher ready (carbon dioxide recommended for diethoxymethane

Procedure (from the same patent example)

Sections

1. Condensation of cyanoacetate and dialkoxymethane 

2. Separation

3. Stabilization

4. Vacuum cracking

5. purification 

Steps: 

1. Add ethyl cyanoacetate and piperidine salt of methanosulfonate to the 4 necked flask

2. Stir

1. No reaction will occur (probably)

3. Set up distillation apparatus (normal pressure) (will be collecting diethoxymethane so take necessary precautions)

1. List of attachments to each neck of the flask

1. Vacuum set-up (Cleison adapter, distillation apparatus, collection flask, etc.)

2. Temperature probe

3. Burette

4. Leave on neck open

4. Raise and maintain temperature at 120°C

5. Add stopper to the fourth neck of the flask

6. Add diethoxymethane dropwise 

1. Reaction will produce ethanol as a byproduct that is immediately distilled

2. Unreacted diethoxymethane will also be distilled

3. The distilled mixture of ethanol and diethoxymethane is still very dangerous and must be disposed of safely.

7. Add methanesulfonic acid and hydroquinone

8. Stir (implied I think)

9. Probably can be cooled to easier-to-use temperatures in this step or in between 5-6 (just for ease setting up the vacuum distillation)

10. Set up vacuum distillation (160° - 200° C / 2.0 mbarr) (collecting crude cyanoacrylate)

11. Distill with the previously set up apparatus (~460g crude cyanoacrylate monomer expected)

12. Set up vacuum distillation (70° - 80° C / 1.5 mbarr)

13. Further distill and purify crude cyanoacrylate to get the finished ethyl cyanoacrylate (~380 g)

Notes:

• Step 4 is probably the most dangerous part of the whole procedure

• Diethoxymethane is highly flammable with a low flashpoint

• Very important to do this part extremely slowly in case of diethoxymethane igniting

• Unreacted diethoxymethane must then be collected and stored (will be collected as diethoxymethane and ethanol, maybe water?)

• NEED TO RESEARCH VACUUM DISTILLATION

• Times for everything?

• Dangers of other chemicals?

• Diethoxymethane is very expensive, will need to downsize experiment a lot because of this

• Disposal of waste stuff (not 100% what will remain after distillation)

• Must assume unreacted chemicals are in any waste including unreacted diethoxymethane

• NOTHING GOES DOWN THE SINK

• Methanosulfonic acid is toxic and extremely corrosive. Avoid breathing in fumes (fume hood always). DONT SPILL.

• Hydroquinone is toxic, carcinogenic, and very dangerous. Keep stored well

Resources:

• How to set up a vacuum distillation (https://www.youtube.com/watch?v=uBoFWSA94kU) 

• How to set up a regular distillation (https://www.youtube.com/watch?v=MNTu5ThnNCQ)

• I took some notes on the setup and am attaching a photo to my journal

• We may need an inert gas to help balance pressure during step 5

Example 3:  full measurements

Materials:

• 564 g (4 mol) n-butyl cyanoacetate

• 8.6 g piperidinium dodecylbenzenesulfonate

• 1200 g (7.5 mol) dibutoxymethane

• 120 mg methanesulfonic acid Sigma Aldrich SDS 

• 0.5 g hydroquinone Sigma Aldrich SDS 

Equipment:

• 2L four-necked flask (rated for vacuum)

• Stirring setup (magnetic stir bar and hot plate)

• Rectification column

• Addition funnel (400-500 mL)

• Temperature probe (ensure compatibility with setup)

• Claisen adapter

• Short-path vacuum distillation apparatus

• Tubing for vacuum and water circulation

• 4 round-bottom flasks (1 neck)

• 2 stoppers

• Pipettes or burette (for controlled addition)

• Vacuum distillation setup (1.5-2.0 mbar, 80-220°C)

Safety Precautions:

• Full-body safety gear required (flame-resistant lab coat, gloves, goggles/face shield).

• Ensure fume hood is operational.

• Have a CO2 fire extinguisher readily available (dibutoxymethane is highly flammable).

• Proper chemical storage (hydroquinone is toxic and carcinogenic; methanesulfonic acid is highly corrosive).

• No disposal of waste into the sink; collect and dispose of according to safety protocols.

Procedure:

1. Condensation Reaction:

• Add 564 g n-butyl cyanoacetate and 8.6 g piperidinium dodecylbenzenesulfonate to the 2L four-necked flask.

• Stir until homogenized.

• Set up rectification column for continuous removal of butanol.

• Attach the temperature probe, addition funnel, and distillation setup (one neck remains open for now).

• Begin heating to 125-127°C.

• Gradually add dibutoxymethane dropwise.

• Maintain temperature and allow the reaction to proceed for 4.5 hours while separating the butanol.

2. Acidification & Stabilization:

• Add 120 mg methanesulfonic acid and 0.5 g hydroquinone.

• Stir thoroughly.

• Allow the reaction mixture to cool to an easier-to-handle temperature.

3. Vacuum Distiliation:

• Set up vacuum distillation (170-220°C / 2 mbar).

• Distill off ~475 g of crude n-butyl cyanoacrylate monomer.

      4. Purification:

• Further distill the crude product under vacuum (80-95°C / 1.5 mbar).

• Collect ~420 g of purified n-butyl cyanoacrylate (99.1% purity, 68% yield).

Notes:

• The most hazardous step is the controlled addition of dibutoxymethane due to its high flammability. We have to add it slowly to prevent ignition.

• Collected butanol and unreacted dibutoxymethane must be handled properly; they can be separated via rectification.

• Research proper vacuum distillation techniques and confirm safe disposal methods for all byproducts.

pressure/boiling point tool 

A Versatile Method of Ambient-Temperature Solvent Removal 

Since butyl cyanoacrylate is susceptible to polymerization and degradation at high temperatures, using a low-temperature solvent removal approach might help preserve the purity of the final product.