During July 1940, Khalutin served as commander of 249 IAP, which was equipped with Polikarpov I-153s.

On 7 July, six Ju 88s, escorted by four Bf 109s, unexpectedly attacked Vinnitsa. The Ju 88s dropped small calibre fragmentation bombs on the airfield and fired with machine-guns at aircraft parked on the runway. The Soviet I-16s on readiness, from the 4th eskadrilya, 88 IAP, attempted to take off to intercept the attackers. Leytenant Semyon Mednik started first, but while trying to gain altitude, he was attacked from behind and shot down by an enemy fighter. Seeing their comrade falling back in flames, the other I-16s postponed their take off. Immediately after the German aircraft left the area, five I-16s, led by the commander of the 4th eskadrilya, Kapitan Polyanskiy, hurriedly took off in pursuit of the enemy. They managed to catch up and attack the German bombers. Close to Yuzhvin (today Nekrasovo) one Ju 88 was brought down by Polyanskiy while two other Ju 88s were claimed by Leytenant Piskunov. One of the 12 I-153s of 249 IAP, which took off to help their neighbours, shot down another bomber. This latter victory was credited to the commander of 249 IAP, Khalutin.
The Ju 88-equipped KG 51 lost three of its bombers. Ju 88A-5 W.Nr. 6231, 9K+BK, off 2./KG 51, failed to return from a mission. Eventually, the pilot and observer returned to their unit, but the others are still listed as missing. 6./KG 51, lost two more Ju 88A-5s. Both were posted as missing in action, also at an unknown location. Days later, only one wounded crewmember returned.

On 7 September 1941, Khalutin claimed a Bf 109 flown by Oberfeldwebel Heinrich Brenner of JG 3 over Mironovka.

Khalutin ended the war with one biplane victory and a total of 2.

Claims:

Kill no.	Date	Time	Number	Type	Result	Plane type	Serial no.	Locality	Unit
	1941
1	07/07/41		1	Ju 88 (a)	Destroyed	I-153		Yuzhvin area	249 IAP
2	07/09/41		1	Bf 109 (b)	Destroyed	I-16		Mironovka	249 IAP

Biplane victories: 1 destroyed.
TOTAL: 2 destroyed.
(a) Possibly claimed in combat with Ju 88s from KG 51 which lost five aircraft while the Soviet fighters from 88 and 249 IAPs claimed four.
(b) Oberfeldwebel Heinrich Brenner of JG 3 KIA.

Sources:
From Barbarossa to Odessa: Volume 1 – Dénes Bernád, Dmitriy Karlenko and Jean-Louis Roba, 2007 Ian Allan Publishing Ltd, ISBN 978-85780-273-3
Additional information kindly provided by Ondrej Repka.