I cannot send email to my personal hotmail account in outlook using my company email id in Outlook

Hi @Asim Zaman-Linkers Chemicals 
Thanks for reaching out to the Microsoft Q&A forum.  

Please understand that our forum is a public platform, and we will modify your question to cover your organization domain name in the description. Please notice to hide these personal or organization information next time you post error or some information to protect personal data. 

Based on your description, it sounds like you're receiving the error message "None of your email accounts could send to this recipient" when trying to send an email from your work Outlook account to your Hotmail address. 

To better assist you, could you please help clarify the following: 
1.Did this issue just start recently, or has it been happening since the beginning? 

2.Does the issue occur across other platforms such as Outlook on the web, the New Outlook, or the Outlook mobile app? 

3.Is the issue specific to this Hotmail account, or does it happen with other recipients or senders as well? 

In the meantime, here are a few troubleshooting steps you can try: 
1.Remove and Re-add the Hotmail Contact 
If the Hotmail address is saved as a contact in Outlook, try removing it and then sending a test email. If the email goes through, you can re-add the contact afterward. 
Sometimes, simply removing and re-adding a contact can refresh the setup and resolve unexpected issues with sending emails. 

2.Open Outlook in Safe Mode: press Window + R > Type Outlook.exe /safe > click OK.   
This helps determine if the issue is related to add-ins or custom settings.   

3.Create a new Outlook profile 
A fresh profile can help rule out any corruption in your current setup. You can follow Microsoft’s guide here:  Create an Outlook profile - Microsoft Support 

Please know that while our initial response might not resolve the issue right away, your input is incredibly valuable. With a bit more detail, we’ll work together to find the best solution for you.  

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I have 2 hotmail accounts and 1 work email id in same outlook.

Issue is only to send to 1 of the hotmail accounts not the other.

As soon as I click send the message returns to inbox and it seems outlook is not even trying to connect to server.

Already tried 1) and 2) above and issue is persisting. The issue has been going for a few months now.