I have a friend who just got the final divorce decree. He has to pay 70% of his income to his ex, leaving him $1400 a month to survive on and raise his teenage daughter. I'm trying to give him some hope and thought of this. He has to pay her half of the value of his company. Is this an expense that he pays through the company (as it is afterall, a business expense) or is this going to have to be paid through his personal account. The company doesn't have a lot of extra per month, but certainly more than his personal account.

Alimony(personal expense) is taxable income for the recipient and is a tax deduction for the payer;your bud who pays alimony reports this amount as a deduction on Form 1040 Line 31.
If you own your own business and need to use funds in your business account to cover personal expenses, it's tempting to simply issue checks from the business account to cover the personal expenses, but it's not a good idea to do so. Depending on the structure of your business, using a business checking account to cover personal expenses may negate the protection the legal structure of your business offers.