Method of producing 1,4-diketo-pyrrolo-(3,4-c)-pyrroles

专利摘要:

公开号:SU1225489A3
申请号:SU833595551
申请日:1983-05-16
公开日:1986-04-15
发明作者:Клод Роша Ален；Кассар Луиджи；Игбал Абул
申请人:Циба-Гейги Аг. (Фирма)；
IPC主号:

专利说明:

The invention relates to a process for the preparation of 1 ,, 4-diketo-pyrrolo- (3,4-c) - -pyrpy. Of the general formula
RI O
oh yag
where R and Rj - independently of
other means unsubstituted or substituted by one or two chlorine atoms, a bromine atom, one or two methyl groups, - | -Pe t-butyl, methoxycyano-, trifluoromethyl-, N-dimethyl-amino-, methyl mercapto-, phenyl-mercapto- phenoxy, cyanophenyl, or 1-pyrryl group phenyl, diphenyl, naphthyl pyridyl, furanyl or thiofuranyl,
which are valuable
pigments.
The aim of the invention is to increase the yield as well as expand the range of business products.
The invention is illustrated by the following examples.
I
Example 1. If possible, a solution consisting of 48.2 ml of tert-amyl alcohol, 17.3 g of t-potassium butylate and 72.2 g of benzonitrile freed from the presence of water was heated under nitrogen to approximately 98 C. Upon reaching the specified temperature, the mixture was added with a dosing pump for 145 minutes. the possibility of a free from the presence of water solution of 7.31 g of dimersual ester of 5.0 md t-amyl alcohol. The temperature was constantly maintained at 98-99 ° C. The resulting methyl alcohol was distilled off. Upon completion of the addition, the reaction mixture was additionally kept at 99 ° C for 2 hours. Immediately after this, the reaction mixture was cooled to 65 ° C. Was slowly diluted with 100 ml of methyl alcohol, neutralized slowly.
10.8 ml of glacial acetic acid, after which the mixture was briefly heated at reflux temperature. The resulting pigment suspension was filtered at C, the filtered product was suspended in 300 ml of methyl alcohol, after which the pigment was filtered again. Then the product was washed to a colorless state with washing water with methyl alcohol and water, and dried in vacuum at 80 ° C. In the result, 9.04 g were obtained (62.8% of the theory based on dimethyl ether
hsfnoy acid) pure pigment
(Iv)
: go
nm
five
0
five
0
five
0
five
which, when introduced into polyvinyl chloride, gave a red color.
Instead of dimethyl ester of succinic acid, without the appearance of specific drawbacks, diethyl succinic ester can be used.
Example 2. 23 g of potassium potassium butyl acetate was suspended in 100 ml of dry tert-amyl alcohol and gradually dissolved. Then, 20.6 g of benzonitrile was added to the prepared solution, and the mixture was heated to approximately 97 ° C. Upon reaching the specified temperature, a solution consisting of 23.0 g of dihydrogen was added to the mixture with stirring for 3 1/4 h. - -butyl ester of succinic acid and 10 ml of "t - -amyl alcohol. The reaction temperature was maintained at 96-98 ° C, and the resulting gret-butyl alcohol was partially distilled off. Upon completion of the addition, the reaction mixture was additionally held for 95 hours at 95-97 ° C, therefore, as in Example 1, the reaction mixture was treated, and instead of 10.8 ml, 13.2 ml of glacial acetic acid was used. After drying in vacuum at 80 ° C, 17.6 g of pure pigment of the formula IV was obtained (60.9% of theory per applied ester). From the queen cell
regenerated benzonitrile, which did not enter into the interaction.
Example 3. 4.7 g of sodium were first dissolved in 65 ml of o-butyl alcohol at the boiling point of the mixture with a reflux condenser (97 ° C) for about 5 hours. The solution obtained was cooled to approximately 50 ° C, added to it benzonitrile after which the mixture was heated to 97 ° C. Immediately thereafter, with: With the help of a dosing pump, 23.0 g of di-P-butyl ester of succinic acid was added to the mixture for about 3 hours, while the temperature was constantly maintained at 97 ° C (the boiling point of the reaction mixture). After completion of the addition, the mixture was further maintained for
11/2 h at 97 ° C, and then, analogously to example 1, the treatment was carried out using 12.6 ml of glacial acetic acid instead of 10.8 ml. After drying under vacuum — at 80 ° C., 8.7 g of pure pigment of formula IV was obtained (30.2% of theory per applied ester).
Examples 4-12. 23.0 gt tert-butiate of potassium was suspended in about 95 ml of dry trem-amylovog alcohol and further dissolution was performed by stirring. Immediately i then 0.2 mol of nitrile of the formula was added to the resulting solution, where R is as shown in table. one. The mixture was heated to a temperature, in the table. one . Upon reaching the reaction temperature, a solution consisting of 13.25 ml of succinic acid dimethyl ester and 5 ml of tert-amyl alcohol was added to the mixture using a dosing pump for a certain time (see Table 1) with gentle stirring. The temperature was maintained and the formed methyl alcohol was distilled off. If the mixture became diluted with a small amount of tert-amyl alcohol. Upon completion of the addition, the reaction mixture was further maintained for
2 h at the same temperature, after which the reaction mixture was treated similarly to 1, using 13.2 ml of glacial acetic acid instead of 10.8 ml. After drying in vacuum at 80 ° C, a pigment of the formula was obtained
R o
about R,
where R takes the values shown in Table 1.
Examples 13-41. Under a nitrogen atmosphere, 8.3 ml of sodium and 0.12 g of sodium salt of 5-s-2-acetyl-hexyl sulphate of succinic acid were added to 145 ml of tert-amyl alcohol. The mixture was heated with gentle stirring to 95-102 ° C. Upon melting of the sodium, the emulsion was vigorously stirred for 3-5 hours at 95-102 ° C. The solution obtained by this method was mixed with 0.24 mol of the nitrile of the formula R, -CN or Rj-CN, where R and Rj are identical substituents {examples 13-29), or with 0.12 mol of the nitrile of the formula R, - The CN and 0.12 COLE of the nitrile of the formula Rj-CN, where R and R are different substituents (examples 30-41). Using a dosing pump at a certain reaction temperature, a solution of 1.2 mol of succinic acid di-isopropyl ester in 12 ml of tert-amyl alcohol was added to the mixture at a certain time. The resulting isopropyl alcohol was constantly distilled off. After completion of the addition, the mixture was further kept for 2 hours at the reaction temperature, after which the reaction mixture was worked up as in Example 1. After drying in vacuum at 80 ° C, a pygmy lt of the formula was obtained
And about
I 1 II
ISiH
45
In tab. 2 and 3 shows the pigments obtained by the proposed method, where R and R are the same and different, substituents, respectively.
Example 42. 4.6 g of sodium and 0.1 g of sodium lauryl sulfate, primed as an emulsifier, were vigorously stirred in 117 ml of tert-amyl alcohol at 94-100 ° C until complete dissolution of sodium. After
cooling, 25.6 g of dry dinitrile of isophthalic acid was added to the mixture and then with a dosing pump for 2 hours at 88-92 ° C - a solution containing 13.25 ml of dimethyl ester of succinic acid and 5 ml of TRI-amyl alcohol. The reaction mixture was kept under stirring at 88-92 s, and the resulting methyl alcohol was constantly distilled off. Upon completion of the addition, the reaction mixture was additionally held for 2 hours at 90 ° C and immediately thereafter treated as in Example 1, using 13, 2 ml of glacial acetic acid and honey, 10.8 ml. After drying in vacuum at 80 ° C, 25.5 g (75.5% of theory per dimethyl ef) (succinic acid) pigment of the formula was obtained.
 CN (V)
NH
which, when introduced into polyvinyl chloride, gave a red-orange color.
Example 43. The method was carried out analogously to example 38, however, instead of t-butyl alcohol, instead of tert-amyl alcohol, 20.6 g (60.8% of theory based on ester) of a pigment of formula V was obtained.
Example 44. The method was carried out analogously to example 38, however, TET-amyl alcohol was used as a solvent, and sodium tert-butoxide obtained in situ was used as an alcoholate, and received 22.9% (67.8% of the theoretical value). on ester) pigment of the formula V,
Example 45. 11.5 g of potassium t-t-butylate are placed in 17.4 ml of t-amyl alcohol and 102.6 ml; benzonitrile. The mixture was heated to 100 ° C, after which at this temperature it was stirred for 3 hours (metering pump) with a solution of 11.6 g of succinic acid di-t-butyl ester in 5 ml of tert-amyl alcohol. After over 2 hours
when the reaction mixture was treated as in example 1, ml of acetic acid was used instead of 10.8 ml. After drying in vacuum at 80 ° C, 10.15 g (70.4% of theory per ester) of pure pigment of formula IV was obtained.
Example 46. 11.5 g of tr "t-potassium t-butylate were suspended in B of 53.2 ml of tert-amyl alcohol and the suspension was mixed with 36.8 vtt of benzonitrile. Prepared mixture
heated to 98 ° C, after which at this temperature it was mixed with a solution of 13.6 g of diphenyl ester of succinic acid in 35 ml of benzonitrile for 2 3/4 h. After you keep the mixture for 1 1/2 h at 100 ° C was treated in the same manner as in Example 1, with 10.9 instead of 10. 8 ml of glacial acetic acid were used. After drying under vacuum
: 5 80 s received 1.66 g (IT, 5% of theory per ester) of a pigment of formula IV ...
Example 47 11.5 g of tert-potassium t-butylate were suspended in 100 ml
Q toluene, and then the suspension was heated to 90 ° C. Immediately thereafter, a solution of 6.63 ml of dimethyl ester of succinic acid in 25.6 ml of benzonitrile was added to the suspension over 2 hours. The reaction mixture was further stirred at 90 ° C for 16 hours and then treated as in Example 1, with 7.2 ml of glacial acetic acid being used instead of 10.8 ml. After drying in vacuum at 80 ° C., 2.54 g (17.6% of theory based on ester) of pure pigment of formula IV was obtained.
Example 48 4.6 g of sodium and 0.1 g of sodium lauryl sulfate were placed in 70 ml of t-amyl alcohol. The prepared suspension was heated to reflux (95-100 ° C).
 Then, 20.7 ml of re-tb-T5-SHOD alcohol was added dropwise to the mixture over 2 hours. The mixture was heated at its reflux temperature (95-100 ° С) until complete
5 dissolving metal. After cooling to room temperature, 59.2 g of 4-methylbenzonitrile1 was added to the mixture, followed by
five
five
heating up. Immediately thereafter, a solution of 22.1 g of mono-iso-propyl-mono-tert-butyl succinic ester in 10 ml of tert-amyl alcohol was added to the mixture for approximately 4 hours, while the temperature was maintained at 97-99 ° C. Then the reaction mixture was further stirred for 1 1/2 hours at the same temperature, after which it was treated as in Example 1, with 13.2 ml of glacial acetic acid instead of 10.8 ml. After drying in vacuum at 80 ° C, 15.4 g (48.6% of theory based on ester) of pigment were obtained, which, when introduced into polyvinyl chloride, gave a red color
9 (vi)
Example 49. 4.6 g of TPST-potassium butylate were suspended in 20 ml of 3-methyl-pentanol-3 and the suspension was mixed with 5.94 g of A-dimethylaminophenonitrile. The mixture was heated to 120 ° C and a solution of 2.65 ml of succinic acid dimethyl ester in 6 ml of 3-methylpentanol-3 was added dropwise to it over 2 hours. After 2 hours at 120 ° C, the reaction mixture was treated in the same manner as Example 1, with 2.3 ml of glacial acetic acid being used instead of 10.8 ml. After drying in vacuum at 80 ° C, 0.28 g (3.7% of theory per ester) of pigment was obtained which, when introduced into polyvinyl chloride, gave a blue color
N
(Vii)
Example 50, 23.0 g of tert-potassium t-butylate are suspended in 145 ml of anhydrous α-amyl alcohol and dissolved with stirring. Immediately after this, 12.8 g of trephthalic acid nitrile and 12.8 g of isophthalic acid nitrile were added to the solution. Oiecb was heated to 90 ° C and then a solution prepared from 13.25 ml of succinic acid dimethyl ester and 5 ml was added to it. tert-amyl alcohol, and
the addition was carried out using a dosing pump for 2 1/2 hours, the temperature was maintained at a level and the resulting methyl alcohol was distilled off. After the addition was completed, the reaction mixture was additionally held for 1 1/2 hours at 90 ° C, and then treated in the same manner as in Example 1, with
12.6 ml of glacial acetic acid. After drying in vacuum at 80 ° C, 24.5 g (72.5% of theory per ester) of pigment was obtained which, when introduced into polyvinyl chloride, gave a red color
CN (VIII)
35
40
Example 51. 3.4 g of the pigment obtained in Example 9 and 2.9 g of the pigment obtained in Example 12 in 100 ml of anhydrous dimethylformamide were mixed with 7.43 ml of sodium methylate solution in 30% ( by weight) methyl alcohol. After the mixture was stirred at room temperature for 3/4 h, a solution of 2.52 ml of glacial acetic acid in 60 ml of methyl alcohol was added dropwise to it within 30 minutes, after which the suspension was stirred for several hours at room temperature temperature After filtration, washing and drying, 5.4 g of mixture was obtained.
pigments corresponding to examples 9 and 12.
Example 52. To 1440 ml of dry fppT -amyl alcohol under a nitrogen atmosphere was added 82.8 g of sodium and 1.2 g of the dry salt of bis-2-ethylhexyl ester of sulfo succinic acid, which was used as an emulsifier. The mixture was heated to about and then held at the boiling point of the mixture under reflux until the metal completely dissolved. The resulting solution was cooled to approximately 80 ° C and then mixed with 247.2 g of dry benzonitrile. After that, the mixture was heated to approximately 110 s and 242.4 g of dry, diisopropyl succinate ester was metered in over a period of about 6 hours. At the same time, the resulting isopropyl alcohol was distilled off. After the addition was completed, the reaction was continued for another 2 h, then the mixture was cooled to about and diluted with 1650 ml of methyl alcohol. Then a mixture consisting of 227 ml of glacial acetic acid and 150 ml of methyl alcohol was slowly added, and pigment precipitated. The product was filtered off at approximately 60 ° C and washed successively with 3000 ml of methyl alcohol and 2000 ml of hot water. After drying in vacuum at 70 ° C, 228.3 g (66% of theory per benzonitrile) of the pigment of formula IV was obtained
P and m-e, p 53. The method was carried out analogously to example 48, however, instead of di-iso-propane ester of succinic acid, the following were used: succinic acid dinopenolate of succinic acid; succinic acid di-2-butyl ester; dicyclohexyl ester of succinic acid or di-tert-butyl ester of succinic acid, the yield of a pigment of the formula IV,% of theory based on benzonitrile: 64.9; 65, 2, 71.5; | 75.7 respectively.
Example 54. The method was carried out analogously to example 48, but the amounts of sodium and di-iso-propyl succinic ester used were increased by 30 wt.%, The pigment of formula IV was obtained with a yield of 81.9% of theory based on benzonitrile.
Example 55. 6.9 g of sodium in an atmosphere of argon were placed in 100 ml of toluene and 26.5 g of 2-methylbutanol-2. The mixture was stirred at its reflux temperature (approximately 100 ° C) until the metal was completely dissolved. At 70-80 ° C for 4-5 hours, a mixture consisting of 21 ml of bezonitrile, 23 g of di-butyl succinic ester and 20 ml of toluene was added dropwise to the prepared mixture. Immediately thereafter, the suspension was stirred for about 19 hours at 80-90 ° C, then neutralization was performed at 60 ° C by adding dropwise a mixture of 21 ml of glacial acetic acid and 80 ml of methyl alcohol - for about 1, 5 h, after which the mixture was further stirred for 30 minutes. The pigment suspension was filtered at 60 ° C, the product was first washed with methyl alcohol and then with water until the washing water became colorless. After drying in a vacuum oven at 80 ° C, 23.8 g (82.5% of theory, based on di- - Ret-butyl ester of succinic acid) of pure pigment according to Example 1, were obtained.
Example 56. Under an argon atmosphere, 3.4 g of a 45% (by weight) suspension of sodium in paraffin was placed in 30 ml of toluene. A mixture of 14 ml of benzonitrile, 7.6 g of di-tert-butyl succinate and 27 ml of toluene was added dropwise over about 2 hours. The temperature of the mixture was gradually increased from 20 to 70 ° C. After this, the stirring was continued for about 20 h at 80 ° C for about 20 hours, during which time a precipitate of pigment was released. After neutralization by the addition of 3.6 ml of glacial acetic acid and 27 ml of methyl alcohol to the reaction mixture, the suspension was filtered, the product was washed with acetone and then with water until the washing water became free of solvent. After drying in a vacuum oven at 80 ° C., 5.6 g (58.9% of theory, based on succinic acid di-tert-butyl ester), were obtained.
that of formula IV.
Example 57. The method was carried out anapogically to example 52, however
To neutralize, instead of a mixture of glacial acetic acid and methyl alcohol, an excess amount of 8% (by weight) hydrochloric acid was used, 230 g of drying was obtained (66.5% of the theory in terms of di-aa-prop; sulphate succinic acid ester) pure pigment of formula IV.
Example 58. Under nitrogen atmosphere, 20.6 g of m-potassium per 100 ml of tetrahydrofuran are added. Then 42 ml of benzonitrile are added thereto and the mixture is heated to 69 ° C; a solution of 23 g of di-tert-butyl ether of amber is added in dosage over 4 hours
NMP - N-methylpyrrnold
acid and 80 ml of tetrahydrofuran. The resulting reaction mixture was kept for another 22 hours with reverse cooling (69 ° C), then cooled to room temperature, a solution of 10.3 ml of acetic acid in 90 ml of methanol was slowly (in the "15 min") added, diluted with 100 ml methanol and heated to 50 ° C.
The precipitated pigment is filtered off, washed with cold methanol and then with water, dried in a vacuum oven to obtain a red powder. 20.2 g of compound IV corresponds to 70.0% of theory based on the ester introduced. Table 1
f aC l
/ Y /.
N- A
СНз1СН) 0-)
at"
105-110 3
- 105-110 3
15 (/ -105-110 2.5
SOS)
CH-i I J .- ..
105-110 3
105-110 2.5
Table
56.8 Orange-474/16 000 in-yellow- 509/21 500 .. (№GR) A
you and
Krasny
473/33 000 508/46 500 (В1-ГРА) АЛ
482/18 000 516/22 000 (DMFA)
Red 500/20000
537/24800 toviolet (DMFA)
Burgundy 528/17500
580/15500 (DMFA)
 NMP - N-methylpyrrolidone DMFA - dimethylformamide
Continuation of table 2
g

 V
TSfC-f 7- 90
2 ±
//
 )
to
105-110 2., 5
OK- .
/ H - 105-110 2,5 rze
m. () Na- {V, 105 - BUT 2.5
erz
- "-"
35 Cl- f) - Nvf / - 105--110 2.5 71.4
  W- NzSo- {-

. H 105-110 2.5
ck
// 104 2.5
Table 3
64.1 Red Violet
52.2 Red
(DMFA) A
470/6 700 502/9 500 530/7 200 (DMFA)
471/17 500 504/23 000 (DMFA)
Orange 470/21 800
503/28 000 (DMFA)
Red 470/26 500
504/35 000
(Schr) AA
479/18 400 511/24 000 (DMFA)
- - 472/38 000 505/36 800 (DMFA)
- - 476/21 600 510/27 200 (DMFA)
Orange 477/22 800 510/30 000 (DMFA)
39С1 -) - НЗСО- ()
in - in
//.
/
 -N CO- :: / -105-11 about 2.5 ..46.3 ezr, - "
tt p, //
4lHaC- / C1- / - - in
105-110 2,5 56,4 Burgundy
 DMFA - dimethylformamide; l NI1P - N-methylpyrrolides,
Compiled by And, Bocharova Editor L. Veselovska Tehred O. Sopko Proofreader L. Patay
1971/62
Circulation 379 Subscription
VNIIPI USSR State Committee
for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5
Production and printing company, Uzhgorod, st. Project, 4
Continued table. 3
56.1 maroon
477/24 200 512/32 800 (DMFA)
Red
473/31 900 507/43 800 (DMFA)
475/23 100 509/31 500 (№iP)

权利要求:
Claims (4)
[1]
1. METHOD FOR PRODUCING 1,4-DIKETO-PYRROLO- (3,4-e) -PYRROLES of the general formula independently unsubstituted _ where R ₁ and R ₂ or substituted by one or two chlorine atoms, one or two bromine atoms IU threshing groups, tert butyl, methoxy, cyano, trifluoromethyl, N-dimethylamino, methylmercapto, o- fenilmerk anm, phenoxy, or tsianfenilnoy 1pirrilnoy group phenyl, biphenyl, p-naphthyl, pyridyl, furanyl, or thiofuranyl _g wherein that, in order to increase the yield and expand the range of target products,
1 mol of an asymmetric or symmetric dialkyl ester of succinic acid with 1-18 carbon atoms, a symmetric diaryl or dicyclohexyl ester of succinic acid is reacted with
[2]
2 mol of nitrile of the general formula
R is —CN (II) or R, —CN (III), where R and Rj are the same substituents, or with 1 mol of nitrile of formula (II) and 1 mol of nitrile of formula (III), where R _T and R ₂ are These are various substituents, in an organic solvent in the presence of an alkali metal alcoholate with 1-10 carbon atoms or an alkali metal, as a strong base at 65-120 C, followed by hydrolysis of the resulting compound.
2. The method according to claim 1, about t l and, especially with the fact that secondary or tertiary alcohol is used as a solvent.
[3]
3. The method according to claim 1, characterized in that an alkali metal alcoholate is used as a strong base.
[4]
4. The method according to claim 1, characterized in that an organic acid is used for hydrolysis.
SU „„ 1225489

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CN103857752B|2011-07-29|2016-05-11|富士胶片株式会社|The preparation method of AZOpigments, AZOpigments, the dispersion that contains AZOpigments, coloured composition and ink for ink-jet recording|

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JP5712166B2|2011-07-29|2015-05-07|富士フイルム株式会社|Dispersion containing azo pigment, coloring composition, ink for inkjet recording, and method for producing dispersion|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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CH305482|1982-05-17|

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