Process for Purifying Mesotrione

Abstract

A process for reducing the levels of undesirable impurities in a mesotrione sample is disclosed, said process comprising the steps of:

Description

EXAMPLE 1

This is an example of the solid adsorption treatment (using carbon as adsorbent) of previously isolated mesotrione which had high levels of impurities. The additional purification option of pre-filtration was used in these examples.

TABLE 1
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
1A	Already isolated mesotrione was dissolved	7900	2800	65%
	into a 10% enolate solution at pH 9.5 with
	KOH. The mixture was pre-filtered and
	contacted with 15% carbon for 2.5 hours
	before being filtered and batch crystallized
	following standard lab procedures.
1B	Already isolated mesotrione was dissolved	7400	4500	39%
	into a 10% enolate solution at pH 9.5 with
	KOH. The mixture was pre-filtered and
	contacted with 15% carbon for 2.5 hours
	before being filtered and batch crystallized
	following standard lab procedures.
1C	Already isolated mesotrione was dissolved	7400	2300	69%
	into a 10% enolate solution at pH 9.5 with
	NaOH/acetonitrile. The enolate was pre-
	filtered and contacted with 15% carbon for
	2.5 hours before being filtered and batch
	crystallized following standard lab
	procedures.
1D	Already isolated mesotrione was dissolved	8800	1900	78%
	into a 10% enolate solution at pH 9.5 with
	NaOH/acetonitrile. The enolate was pre-
	filtered and batch carbon treated with 9%
	carbon for 3 hours. The carbon was filtered
	and the enolate was crystallized in a
	continuous reactor following standard lab
	procedures.
1E	Already isolated mesotrione was dissolved	8800	3100	65%
	into a 10% enolate solution at pH 9.5 with
	triethylamine. The enolate was pre-filtered
	and batch carbon treated with 9% carbon
	for 3 hours. The carbon was filtered and
	the enolate was crystallized in a continuous
	reactor following standard lab procedures.
1F	Already isolated mesotrione was dissolved	7900	4600	42%
	into a 10% enolate solution at pH 9.5 with
	NaOH/acetonitrile. The mixture was pre-
	filtered and contacted with 15% carbon for
	2.5 hours before being filtered and batch
	crystallized following standard lab
	procedures.
1G	Already isolated mesotrione was dissolved	7400	4600	38%
	into a 10% enolate solution at pH 9.5 with
	NaOH. The mixture was pre-filtered and
	contacted with 15% carbon for 2.5 hours
	before being filtered and batch crystallized
	following standard lab procedures.

EXAMPLE 2

This is an example of a solvent extraction treatment of previously isolated mesotrione which had high levels of impurities.

TABLE 2
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
2A	Already isolated mesotrione was dissolved	8000	4100	49%
	into a 10% enolate solution at pH 12.5
	with KOH. The mixture was contacted
	with 1,2-dichloroethane, the 1,2-
	dichloroethane was extracted, and the
	remaining aqueous layer was batch
	crystallized following standard lab
	procedures.
2B	Already isolated mesotrione was dissolved	8000	4300	46%
	into a 10% enolate solution at pH 12.5
	with KOH. The mixture was contacted
	with benzonitrile, the benzonitrile was
	extracted, and the remaining aqueous layer
	was batch crystallized following standard
	lab procedures.

EXAMPLE 3

This is an example of an integrated adsorption treatment of in-process mesotrione enolate. NMSBA purified by standard procedures was used as the starting material. The mixture was distilled before the enolate treatments and the purification element of pre-filtration was included. Different adsorbent loadings are shown in the examples in this table.

TABLE 3
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
3A	Mesotrione was made using the standard	13800	11100	20%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 13% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
3B	Mesotrione was made using the standard	13800	5100	63%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 27% carbon for 3.5 hours
	before being filtered and batch crystallized
	following standard lab procedures.
3C	Mesotrione was made using the standard	13800	5700	59%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 40% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
3D	Mesotrione was made using the standard	13800	5800	58%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 53% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
3E	Mesotrione was made using the standard	17900	15900	11%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 5% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
3F	Mesotrione was made using the standard	17900	15000	16%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 10% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
3G	Mesotrione was made using the standard	17900	12300	31%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 20% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.

EXAMPLE 4

This is an example of an integrated adsorption treatment of in process mesotrione enolate. NMSBA purified by standard procedures was used as the starting material. The mixture was distilled before the enolate treatment, and the purification element of pre-filtration was included. Different filtration conditions are used in the examples in this table.

TABLE 4
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
4A	Mesotrione was made using the standard	15800	7400	53%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 7 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 10% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
4B	Mesotrione was made using the standard	15800	7700	51%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 7 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 10% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
4C	Mesotrione was made using the standard	15800	10400	34%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 10% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.
4D	Mesotrione was made using the standard	15800	8600	46%
	process from NMSBA purified by standard
	procedures. After the distillation, an
	enolate solution at pH 9.5 was formed with
	KOH. The mixture was pre-filtered and
	contacted with 10% carbon for 2 hours
	before being filtered and batch crystallized
	following standard lab procedures.

EXAMPLE 5

This is an example of an integrated solvent extraction treatment of in process mesotrione enolate. Crude NMSBA was used as the starting material. The mixture was distilled before the enolate treatment.

TABLE 5
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
5A	Mesotrione was made using the standard	11000	7800	29%
	process from crude NMSBA. After the
	distillation, an enolate solution at pH 13
	was formed with KOH. The mixture was
	contacted with 1,2-dichloroethane, the 1,2-
	dichloroethane was extracted, and the
	remaining aqueous layer was batch
	crystallized following standard lab
	procedures.

EXAMPLE 6

This is an example of an integrated adsorption treatment of in process mesotrione enolate. Partially purified NMSBA was used as the staring material. The mixture was distilled before the enolate treatment.

TABLE 6
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
6A	Mesotrione was made using the standard	13300	6300	53%
	process from partially purified NMSBA.
	After the distillation, an enolate solution at
	pH 5 was formed with NaOH and ACN.
	The mixture was contacted with 20%
	carbon for 2 hours before being filtered and
	batch crystallized following standard lab
	procedures.
6B	Mesotrione was made using the standard	8500	4900	42%
	process from partially purified NMSBA(.
	After the distillation, an enolate solution at
	pH 9 was formed with NaOH and ACN.
	The mixture was contacted with 20%
	carbon for 2 hours before being filtered and
	batch crystallized following standard lab
	procedures.

EXAMPLE 7

This is an example of an integrated column adsorption treatment of in process mesotrione enolate. Crude NMSBA was used as the starting material. The mixture was distilled before the enolate treatment.

TABLE 7
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
7A	Mesotrione was made from crude NMSBA	11400	10500	8%
	following standard lab procedures. After
	the distillation, an enolate solution at pH
	9.5 was formed with KOH. The mixture
	was pre-filtered and sent through a carbon
	column such that there was 14.9% carbon
	usage. Samples were batch crystallized
	following standard lab procedures.
7B	Mesotrione was made from crude NMSBA	11400	10100	11%
	following standard lab procedures. After
	the distillation, an enolate solution at pH
	9.5 was formed with KOH. The mixture
	was pre-filtered and sent through a carbon
	column such that there was 5.08% carbon
	usage. Samples were batch crystallized
	following standard lab procedures.
7C	Mesotrione was made from crude NMSBA	11400	6600	42%
	following standard lab procedures. After
	the distillation, an enolate solution at pH
	9.5 was formed with KOH. The mixture
	was pre-filtered and sent through a carbon
	column such that there was 2.93% carbon
	usage. Samples were batch crystallized
	following standard lab procedures.

EXAMPLE 8

This is an example of an integrated adsorption treatment of in process mesotrione enolate. Purified or crude NMSBA was used as the staring material. TEA decantation is included as a purification element. The mixture was distilled before the enolate treatment

TABLE 8
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
8A	Mesotrione was made from crude NMSBA	11400	5600	51%
	by the standard process. An enolate
	solution at pH 13 was formed with KOH.
	The TEA was decanted, and the enolate
	was contacted with 20% carbon for 2
	hours at pH 9.5 before being filtered and
	batch crystallized following standard lab
	procedures.
8B	Mesotrione was made from crude NMSBA	20600	8900	57%
	by the standard process. After the
	distillation, an enolate solution at pH 13
	was formed with KOH. The TEA was
	decanted, and the enolate was contacted
	with 20% carbon for 2 hours at pH 9.5
	before being filtered and batch crystallized
	following standard lab procedures.
8C	Mesotrione was made from crude NMSBA	15000	6300	58%
	by the standard process. After the
	distillation, an enolate solution at pH 13
	was formed with KOH. The TEA was
	decanted, and the enolate was contacted
	with 20% carbon for 2 hours at pH 9.5
	before being filtered and batch crystallized
	following standard lab procedures.
8D	Mesotrione was made from purified	6300	3400	46%
	NMSBA by the standard process. An
	enolate solution at pH 13 was formed with
	KOH. The TEA was decanted, and the
	enolate was contacted with 20% carbon for
	2 hours at pH 9.5 before being filtered and
	batch crystallized following standard lab
	procedures.
8E	Mesotrione was made from purified	7300	2900	60%
	NMSBA by the standard process. An
	enolate solution at pH 13 was formed with
	KOH after the completion of the solvent
	distillation. The TEA was decanted, and
	the enolate was contacted with 20% carbon
	for 2 hours at pH 9.5 before being filtered
	and batch crystallized following standard
	lab procedures.
8F	Mesotrione was made from purified	6600	3300	50%
	NMSBA by the standard process. An
	enolate solution at pH 13 was formed with
	KOH after the completion of the solvent
	distillation. The TEA was decanted, and
	the enolate was contacted with 20% carbon
	for 2 hours at pH 9.5 before being filtered
	and batch crystallized following standard
	lab procedures.

EXAMPLE 9

This is an example of the effect of the presence of acetonitrile during crystallization on the impurity content of mesotrione. An integrated purification was done which used the purification elements of TEA decant and the presence of acetonitrile during the crystallization. The mixture was distilled before the enolate treatment. Crude NMSBA was used as the starting material.

TABLE 9
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
9A	Mesotrione was made from crude NMSBA	21800	12800	41%
	using the standard process. After solvent
	distillation, a potassium enolate solution at
	pH 13 was made and the TEA was
	decanted. The enolate was batch
	crystallized following standard lab
	procedures except that acetonitrile was
	present during the crystallization.
9B	Mesotrione was made from crude NMSBA	21800	12800	41%
	using the standard process. After solvent
	distillation, a potassium enolate solution at
	pH 13 was made and the TEA was
	decanted. The enolate was batch
	crystallized following standard lab
	procedures except that acetonitrile was
	present during the crystallization.
9C	Mesotrione was made from crude NMSBA	30900	9000	71%
	using the standard process. After solvent
	distillation, a potassium enolate solution at
	pH 13 was made and the TEA was
	decanted. The enolate was batch
	crystallized following standard lab
	procedures except that acetonitrile was
	present during the crystallization.

EXAMPLE 10

This is an example of the integrated process starting with crude NMSBA in which a partial NMSBA purification is incorporated directly into the process. The purification elements of decantation and adsorption treatment are used in these examples.

TABLE 10
			Impurities	%
		Original	Content	Reduction
		Impurities	after	in
Example		Content	Treatment	Impurities
No.	Treatment	(PPM)	(PPM)	Content
10A	Mesotrione was made from the integrated	2900	2500	53%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile was
	added to make a NMSBA solution and the
	remaining water was distilled. Inorganic
	salts were filtered from the acid chloride
	after excess phosgene removal. The C/R
	proceeded by normal reaction conditions.
	An enolate solution at pH 13 was formed
	with KOH. The TEA and benzonitrile
	were decanted and the enolate was
	contacted with 20% carbon for 2 hours at
	pH 9.5 before being filtered and batch
	crystallized following standard lab
	procedures.
10B	Mesotrione was made from the integrated	2900	1100	62%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile was
	added to make a NMSBA solution and the
	remaining water was distilled. Inorganic
	salts were filtered from the acid chloride
	after excess phosgene removal. The C/R
	proceeded by normal reaction conditions.
	An enolate solution at pH 13 was formed
	with KOH. The TEA and benzonitrile
	were decanted and the enolate was
	contacted with 20% carbon for 2 hours at
	pH 9.5 before being filtered and batch
	crystallized following standard lab
	procedures.
10C	Mesotrione was made from the integrated	2900	2100	28%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile was
	added to make a NMSBA solution and the
	remaining water was distilled. Inorganic
	salts were filtered from the acid chloride
	after excess phosgene removal. The C/R
	proceeded by normal reaction conditions.
	An enolate solution at pH 13 was formed
	with KOH. The TEA and benzonitrile
	were decanted and the enolate was
	contacted with 20% carbon for 2 hours at
	pH 9.5 before being filtered and batch
	crystallized following standard lab
	procedures.
10D	Mesotrione was made from the integrated	2900	1600	45%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile was
	added to make a NMSBA solution and the
	remaining water was distilled. Inorganic
	salts were filtered from the acid chloride
	after excess phosgene removal. The C/R
	proceeded by normal reaction conditions.
	An enolate solution at pH 13 was formed
	with KOH. The TEA and benzonitrile
	were decanted and the enolate was
	contacted with 20% carbon for 2 hours at
	pH 9.5 before being filtered and batch
	crystallized following standard lab
	procedures.
10E	Mesotrione was made from the integrated	2900	1900	34%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile
	was added to make a NMSBA solution
	and the remaining water was distilled.
	Inorganic salts were filtered from the acid
	chloride after excess phosgene removal.
	The C/R proceeded by normal reaction
	conditions. An enolate solution at pH 13
	was formed with KOH. The TEA and
	benzonitrile were decanted and the enolate
	was contacted with 20% carbon for 2
	hours at pH 9.5 before being filtered and
	batch crystallized following standard lab
	procedures.
10F	Mesotrione was made from the integrated	2900	1500	48%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water at pH 0.8.
	Benzonitrile was added to make a 20%
	NMSBA solution and the remaining water
	was distilled. Inorganic salts were filtered
	from the acid chloride after excess
	phosgene removal. The C/R proceeded by
	normal reaction conditions. An enolate
	solution at pH 13 was formed with KOH.
	The TEA and benzonitrile were decanted
	and the enolate was contacted with 20%
	carbon for 2 hours at pH 13 before being
	filtered and batch crystallized following
	standard lab procedures.
10G	Mesotrione was made from the integrated	4900	3100	37%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile
	was added to make a NMSBA solution
	and the remaining water was distilled.
	Inorganic salts were filtered from the acid
	chloride after excess phosgene removal.
	The C/R proceeded by normal reaction
	conditions. An enolate solution at pH 13
	was formed with KOH. The TEA and
	benzonitrile were decanted and the enolate
	was contacted with 20% carbon for 2
	hours at pH 9.5 before being filtered and
	batch crystallized following standard lab
	procedures.
10H	Mesotrione was made from the integrated	3200	2500	22%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile was
	added to make NMSBA solution and the
	remaining water was distilled. Inorganic
	salts were filtered from the acid chloride
	after excess phosgene removal. The C/R
	proceeded by normal reaction conditions.
	An enolate solution at pH 13 was formed
	with KOH. The TEA and benzonitrile
	were decanted and the enolate was
	contacted with 20% carbon for 2 hours at
	pH 9.5 before being filtered and batch
	crystallized following standard lab
	procedures.
10I	Mesotrione was made from the integrated	3200	2000	38%
	process starting with crude NMSBA in
	water which was partially purified and
	distilled to remove water. Benzonitrile was
	added to make a NMSBA solution and the
	remaining water was distilled. Inorganic
	salts were filtered from the acid chloride
	after excess phosgene removal. The C/R
	proceeded by normal reaction conditions.
	An enolate solution at pH 13 was formed
	with KOH. The TEA and benzonitrile
	were decanted and the enolate was
	contacted with 20% carbon for 2 hours at
	pH 9.5 before being filtered and batch
	crystallized following standard lab
	procedures.

EXAMPLE 11

Previously isolated mesotrione, made from crude NMSBA, was dissolved by addition of dilute potassium hydroxide to form a 9.1% w/w solution of potassium enolate at pHs 7, 9.5 and 11, respectively. The very small amount of residual solid was removed by filtration.

Extraction

The aqueous solution of potassium enolate of mesotrione (183 g) was extracted with solvent (150 ml) four times. The phases were separated after each extraction and the solvent phase was discarded. After the fourth extraction, the mesotrione was recovered from the aqueous phase by continuous crystallisation according to standard procedure. Analysis showed reduction of the impurities (Table 11A). The figures in parenthesis are the percentage of the impurities remaining after treatment.

	TABLE 11A
	Sum of impurities in mesotrione sample (%)
Solvent	Before	After pH 7	After pH 9.5	After pH 11
MIBK	3.419	0.258 (7.55%)	1.305 (38.2%)	1.308 (38.3%)
Ethyl acetate	3.419	1.997 (58.4%)	1.941 (56.8%)	2.098 (61.4%)
Benzonitrile	3.419	1.991 (58.2%)	1.018 (29.8%)	1.652 (48.3%)
2-	5.627	0.182 (3.2%)	1.361 (24.2%)	1.217 (21.6%)
ethylhexanol

Adsorption

The aqueous solution of potassium enolate of mesotrione (183 g) was stirred with 5 g adsorbent at ambient temperature (˜25° C.) for 30 minutes. The adsorbent was removed by filtration and the mesotrione was recovered from the aqueous phase by continuous crystallisation according to standard procedure. Analysis showed reduction of the impurities (Table 11B). The figures in parenthesis are the percentage of the impurities remaining after treatment.

	TABLE 11B
	Sum of impurities in mesotrione sample (%)
Adsorbent	Before	After pH 7	After pH 9.5	After pH 11
Ambersorb	5.627	0.383 (6.81%)	0.680 (12.1%)	0.171 (3.04%)
348F
Amberlite	5.627	0.892 (15.9%)	1.692 (30.1%)
XAD4
Amberlite	3.419	0.245 (7.17%)	0.063 (1.84%)	0.145 (4.24%)
XAD16
Molecular	5.627	1.414 (25.1%)		1.792 (31.8%)
sieves 5A

Claims

1. A process for reducing the levels of undesirable impurities in a mesotrione sample, said process comprising the steps of: (i) forming a mesotrione enolate solution in an aqueous solvent,(ii) carrying out one or more purification processes, and(iii) crystallising the purified mesotrione out of solution.

2. A process according to claim 1, wherein the process further comprises a distillation step.

3. A process according to claim 1, wherein the one or more purification processes are selected from the group consisting of filtration, adsorption treatment, extraction with an organic solvent, and decantation.

4. A process for reducing the levels of undesirable impurities in a mesotrione sample, said process comprising: a distillation step, formation of a mesotrione enolate solution; one or more purification steps; and crystallisation of mesotrione.

5. A process for reducing the levels of undesirable impurities in a mesotrione sample, said process comprising: formation of a mesotrione enolate solution; decantation, filtration and adsorption treatment carried out in any order; and crystallisation of mesotrione.

6. An integrated manufacturing/purification process for mesotrione, said process comprising the steps of: (i) reacting cyclohexanedione with 2-nitro4-methylsulphonyl benzoyl chloride (NMSBC) to form an enol ester followed by a rearrangement process to give mesotrione;(ii) formation of mesotrione enolate in aqueous solution;(iii) carrying out one or more purification processes, and(iv) crystallising the purified mesotrione out of solution.

7. A process according to claim 6, wherein said process further comprises a distillation step.

8. A process according to claim 6 or, wherein the NMSBC is first subjected to a carbon purification treatment.

9. An integrated manufacturing/purification process for mesotrione, said process comprising: reacting cyclohexanedione with 2-nitro-4-methylsulphonyl benzoyl chloride (NMSBC) to form an enol ester followed by a rearrangement process to give mesotrione; a distillation step; formation of a mesotrione enolate solution; one or more purification steps; and crystallisation of mesotrione.

10. An integrated manufacturing/purification process for mesotrione, said process comprising reacting cyclohexanedione with 2-nitro-4-methylsulphonyl benzoyl chloride (NMSBC) to form an enol ester followed by a rearrangement process to give mesotrione; formation of a mesotrione enolate solution; decantation, filtration and adsorption treatment, carried out in any order; and crystallisation of mesotrione.

11. A process for preparing mesotrione, said method comprising: (i) Oxidation of NMST to give crude NMSBA;(ii) conversion of NMSBA to NMSBC;(iii) reacting cyclohexanedione with 2-nitro-4-methylsulphonyl benzoyl chloride (NMSBC) to form an enol ester followed by a rearrangement process to give mesotrione;(iv) formation of mesotrione enolate in aqueous solution;(v) carrying out one or more purification processes, and(vi) crystallising the purified mesotrione out of solution.

12. The method of claim 11, wherein the process further comprises partial purification of the crude NMSBA.

13. The method of claim 11, wherein the process further comprises a distillation step.

14. A process for preparing mesotrione, said process comprising: oxidation of NMST to give crude NMSBA; optional partial purification of crude NMSBA; conversion of NMSBA to NMSBC; reacting cyclohexanedione with 2-nitro-4-methylsulphonyl benzoyl chloride (NMSBC) to form an enol ester followed by a rearrangement process to give mesotrione; a distillation step; formation of potassium enolate mesotrione solution; one or more purification steps; and crystallisation of mesotrione.

15. A process for preparing mesotrione, said process comprising: oxidation of NMST to give crude NMSBA; optional partial purification of crude NMSBA; conversion of NMSBA to NMSBC; reacting cyclohexanedione with 2-nitro-4-methylsulphonyl benzoyl chloride (NMSBC) to form an enol ester followed by a rearrangement process to give mesotrione; formation of a mesotrione enolate solution; decantation, filtration and adsorption treatment carried out in any order; and crystallisation of mesotrione.