Question about start a 450kW pump

Can I start a 450KW pump from the grid using star-delta and then use a bypass contactor to switch to an already running generator of 500kVA in order to avoid the starting current?

In my opinion, this operation is very dangerous. 500kVA is usually Diesel generator and interaction between load and source is very high.

Although maybe reduced starting current by means of your proposed figure but following comment shall be take in to account:
• The distance between load and generator is important
• Difference phase angle between grid and 500kVA generator possible to generate torsional effect and it is harmful for rotor in transfer moment
• Reacceleration is very important situation and maybe stall the motor
• Voltage dip due to starting another motor can make disturbance and this network is very weak respect to transient phenomena
• De-rating of generator maybe cause to have 70% or less then nominal rating of name plate (based on site elevation, ambient temperature and humidity)
• Meanwhile power absorption by electrical motor (450 kW) is more than generator normal capacity (500kVA).
As wrap up it is not safe and operational case

Actually I think it won't work:
1). At 450 kw of a load is already bigger that the capacity of the Generator which is 500kva. (considering the pf of 20% the genset capacity is 400 kw which is way below even the maximum continuous power consumption of the load -450kw).

If your client had say 550KW GENSET, then I would definitely give him a solution which is sustainable. He just doesn’t even have to start the pump with the grid power then cross to Genset. We can propose an equipment that can give a smooth start of the motor and ration supply of power to the motor depending on the load requirement (the energy required to do a certain activity)

Soft Start and Soft Stop - When starting, an AC Induction motor develops more torque than is required at full speed. This stress is transferred to the mechanical transmission system resulting in excessive wear and premature failure of chains, belts, gears, mechanical seals, etc.

Additionally, rapid acceleration also has a massive impact on electricity supply charges with high inrush currents drawing +600% of the normal run current. The use of Star Delta only provides a partial solution to the problem. Should the motor slow down during the transition period the high peaks are repeated and can even exceed direct on line current. THE EQUIPMENT WE CAN PROPOSE provides a reliable and economical solution to these problems by delivering a controlled release of power to the motor, thereby providing smooth, stepless acceleration and deceleration. Motor life will be extended as damage to windings and bearings is reduced.

-Less mechanical stress.
-Improved power factor.
-Lower maximum demand.
-Less mechanical maintenance.

Soft Start and Soft Stop is especially useful with pumping fluids where torque transients often cause water hammer effects, and in some instances, failure to gradually slow the fluid down before stopping, can cause the kinetic energy to rupture pipes and couplings.