CN110183336A - A kind of preparation method of 3- amino -4- cetyl chlorobenzoate - Google Patents
A kind of preparation method of 3- amino -4- cetyl chlorobenzoate Download PDFInfo
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- CN110183336A CN110183336A CN201910497260.7A CN201910497260A CN110183336A CN 110183336 A CN110183336 A CN 110183336A CN 201910497260 A CN201910497260 A CN 201910497260A CN 110183336 A CN110183336 A CN 110183336A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
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Abstract
The present invention is a kind of preparation method of 3- amino -4- cetyl chlorobenzoate.This method comprises the following steps: 3- amino -4- chlorobenzoic acid and positive hexadecanol being added in water entrainer, are heated to 50oC, 0.5 ~ 1 h of constant temperature, adds catalyst p-methyl benzenesulfonic acid, continues to be heated to 140 ~ 170oC reacts 6 ~ 12 h at reflux, stops heating；Organic solvent is added in the reaction solution obtained one step up, then crystallisation by cooling, washing, filtering, obtains crude product after filter cake is dried；Filtrate is collected；Organic solvent is added in crude product, dissolves by heating, crystallisation by cooling, filtering；Finished product 3- amino -4- cetyl chlorobenzoate is obtained after filter cake is dried；The present invention improves the utilization rate of raw material, improves product yield, reduces the treating capacity of industrial filtrate, reduces industrial production cost, be more favorable for industrialized production.
Description
Technical field
Present document relates to the synthesis of the synthetic method of organic compound more particularly to 3- amino -4- cetyl chlorobenzoate is new
Route belongs to aliphatic ester synthesis technical field.
Background technique
3- amino -4- cetyl chlorobenzoate is novel DIR yellow colour coupler intermediate, which makes color sensitive material
Reactivity with higher, oil-soluble, color development density reduce granularity, improve clarity and saturation degree.
Currently, there are two types of raw material routes on 3- amino -4- cetyl chlorobenzoate: first is that with 3- amino -4- chlorobenzoic acid
It is reacted with bromohexadecane；Second is that being reacted with 3- amino -4- chlorobenzoic acid and positive hexadecanol.The first raw material route reaction condition
Mildly, reaction speed is fast, product yield high, purity is high, but the expensive improper industrialized production of bromohexadecane.
Second of raw material route is the emphasis of current industrial research.Japan Patent JP 9286766 is catalysis with the concentrated sulfuric acid
Agent, reactivity are high, but it is serious to equipment corrosion, by-product is more, post-processing trouble, while alcohol dosage is 3 times of acid, not instead
Alcohol separation, the recycling answered are difficult, and sterling purity is 95.00%；Sour four chlorinations of catalyst Lewis of Chinese patent CN 1974543
Tin replaces the concentrated sulfuric acid, overcomes the technical problems such as by-product is more, alcohol dosage is more, yield 70.00%, purity 98.50%.But
Tin tetrachloride meets water decomposition, generates corrosive gas HCl and positive stannic acid, and the requirement to equipment is high, positive stannic acid separation is difficult.Always
It, all recycles water entrainer by the way of vacuum distillation in Article 2 raw material route, and post-processing operation is cumbersome, meanwhile, in the process
A large amount of by-products, which can be generated, makes product separation propose difficulty increasing.
Summary of the invention
Patent of the invention be to overcome in prior art route alcohol dosage is more, by-product is more, product separating-purifying is difficult,
The Industrialized processing techniques problem such as severe corrosion to equipment and production cost height provides a kind of 3- amino -4- chlorobenzoic acid 16
The preparation method of ester.This method uses p-methyl benzenesulfonic acid for catalyst, and toluene/xylene mixture solvent is water entrainer, and is added
Organic solvent crystallisation by cooling step, simplifies original process route.The present invention improves the utilization rate of raw material, improves product yield,
The treating capacity and industrial production cost for reducing industrial filtrate, are more favorable for industrialized production.
The technical solution of the invention is as follows:
A kind of preparation method of 3- amino -4- cetyl chlorobenzoate, includes the following steps:
1. 3- amino -4- chlorobenzoic acid and positive hexadecanol are added in water entrainer, 50 DEG C, 0.5~1h of constant temperature are heated to,
Catalyst p-methyl benzenesulfonic acid is added, continues to be heated to 140~170 DEG C, reacts 6~12h at reflux, stops heating；
Wherein, water entrainer is toluene/xylene mixture solvent, the mass fraction of toluene be mixed solvent 10%~
50%；N (positive hexadecanol): n (3- amino -4- cetyl chlorobenzoate)=1.0~1.2:1；Water entrainer quality is 3- amino -4-
1.0~2.5 times of chlorobenzoic acid quality；Catalyst p-methyl benzenesulfonic acid and 3- amino -4- chlorobenzoic acid molar ratio be 0.06~
0.12:1；
2. organic solvent is added in the reaction solution obtained one step up, then crystallisation by cooling, washing, filtering, filter cake is dried
Crude product is obtained after dry；Filtrate is collected；
Wherein, organic solvent is methanol, and dosage is 5~10 times of water entrainer quality；
3. organic solvent is added into crude product, dissolve by heating, crystallisation by cooling, filtering；Finished product is obtained after filter cake is dried
3- amino -4- cetyl chlorobenzoate, filtrate are collected；
The organic solvent is methanol, and dosage is 5~10 times of water entrainer quality；
4. by step 2. and 3. in filtrate decompression be concentrated into 0.02~0.05 times of original filtrate volume；In concentrate
Distilled water, crystallisation by cooling is added, filtering removal catalyst obtains regenerant after drying filter cake；It include unreacted in regenerant
Raw material and portion of product；The dosage of the distilled water is 5~10 times of water entrainer dosage；
5. regenerant, 3- amino -4- chlorobenzoic acid and positive hexadecanol are added in water entrainer, 50 DEG C are heated to, constant temperature
0.5~1h adds catalyst p-methyl benzenesulfonic acid, continues to be heated to 140~170 DEG C, reacts 6~12h at reflux, stops
Only heat；
The water entrainer, catalyst and step 1. in composition it is identical with dosage；3- amino -4- chlorobenzene the first being newly added
Sour and positive hexadecanol gross mass is 3. quality that step obtains finished product 3- amino -4- cetyl chlorobenzoate, and n (positive 16
Alcohol): n (3- amino -4- cetyl chlorobenzoate)=1.0:1；
6. organic solvent is added after esterification, crystallisation by cooling, washing, filtering, filter cake is dried after slightly produced
Object；
7. organic solvent is added into crude product, dissolve by heating, crystallisation by cooling, filtering；Finished product is obtained after filter cake is dried
3- amino -4- cetyl chlorobenzoate, filtrate are collected.
The step organic solvent that 6. middle recrystallization purifies is methanol, and dosage is 5~10 times of water entrainer quality.
7. middle filtrate recycling obtains crude product to recrystallize the organic solvent purified being isopropanol step with reuse, uses
Amount is 3~8 times of water entrainer quality.
Substantive distinguishing features of the invention are as follows:
The present invention uses toluene/xylene mixture solvent for water entrainer, compared with single water entrainer dimethylbenzene, reduces anti-
Object temperature is answered, the difference of esterification yield and one-way yield is reduced, improves one-way yield；And it devises unreacting material in filtrate
The process flow reused after recycling improves the utilization rate of raw material, improves product yield, reduces the treating capacity of industrial filtrate,
Industrial production cost is reduced, industrialized production is more favorable for.
The invention has the benefit that
The present invention use catalytic activity it is high, selectivity it is good, to the non-corrosive p-methyl benzenesulfonic acid of equipment for catalyst close
At 3- amino -4- cetyl chlorobenzoate, by-product is reduced, product purity improves, equipment requirement reduces.
(2) use toluene/xylene mixture solvent as water entrainer with single solvent dimethylbenzene compared with water entrainer, reduce
Reaction temperature, reduces the difference of conversion ratio and yield, improves yield.
(3) the molar ratio of positive hexadecanol and 3- amino -4- chlorobenzoic acid is reduced to 1.0~1.2:1, simplify product separation with
The process flow of purification, improves product yield and purity.
(4) post-processing is dissolved in unreacting material in filtrate, by being reused after vacuum distillation concentration and recovery, product
Yield up to 82.54%, yield improves 12.54% compared with CN 1974543.The design of this process flow improves raw material
Utilization rate, improve the yield of product, reduce the treating capacity and industrial production cost of industrial filtrate.
Specific embodiment
3- amino -4- cetyl chlorobenzoate is the intermediate of novel DIR yellow colour coupler, for dropping in color sensitive material
Low granularity, raising resolving power, raising clarity and saturation degree, colour picture are more clear, are bright-coloured.
The present invention provides the new synthesis route of 3- amino -4- cetyl chlorobenzoate, raw material 3- amino -4- chlorobenzoic acids
With positive hexadecanol under the action of catalyst p-methyl benzenesulfonic acid and water entrainer lactate synthesis 3- amino -4- cetyl chlorobenzoate.
Wherein toluene/xylene mixture solvent is water entrainer, makes to react mobile to the direction for generating product by reflux dewatering, by going out
Water judges reaction end, reaction easy to control.
It illustrates below and specific description is done to the present invention program.
Embodiment 1: be equipped with thermometer, water segregator, stirring rod three-necked flask in be separately added into 156g (0.91mol)
3- amino -4- chlorobenzoic acid, 264g (1.09mol) positive hexadecanol, 28g toluene, 252g dimethylbenzene, are heated with stirring to 50 DEG C, perseverance
The p-methyl benzenesulfonic acid of 15.6g (0.091mol) is added in warm 0.5h after positive hexadecanol is completely dissolved, and continues heating in reflux temperature
8h is reacted at 156~164 DEG C, stops reaction, the methanol of 1500mL is added, is cooled to 20 DEG C, crystallization time 5h, and filtering will filter
Crude product 272g is obtained after cake drying, is collected into 1500mL first time filtrate.1500mL methanol is added in crude product, is heated to 70
DEG C wait be completely dissolved, 10 DEG C are cooled to, recrystallizes time 8h, filtering obtains 264g finished product 3- amino -4- chlorine after drying filter cake
Benzoic acid hexadecyl ester, yield 73.26% are collected into second of filtrate of 1500mL.HPLC test analysis 3- amino -4- chlorobenzoic acid
The purity of hexadecyl ester is 98.30%.
2. and 3. first time filtrate and second of filtrate (about 3000mL) that step is collected is concentrated by vacuum distillation
80mL is added 1500mL distilled water crystallisation by cooling, removes catalyst after filtering, and regenerant is obtained after filter cake is dried, and 109g is added
(0.64mol) 3- amino -4- chlorobenzoic acid, 155g (0.64mol) positive hexadecanol, 28g toluene, 252g dimethylbenzene, agitating and heating
To 50 DEG C, constant temperature 0.5h, the p-methyl benzenesulfonic acid of 15.6g (0.091mol) is added after positive hexadecanol is completely dissolved, continues to heat
8h is reacted at 156~164 DEG C of reflux temperature, stops reaction, the methanol of 1500mL is added, is cooled to 20 DEG C, crystallization time 5h,
Filtering, obtains 240g crude product after filter cake is dried.800mL isopropanol is added in crude product and is heated to 75 DEG C wait be completely dissolved,
5 DEG C are cooled to, time 6h is recrystallized, filtering obtains 225g finished product 3- amino -4- cetyl chlorobenzoate after drying filter cake,
Yield 69.29%.The purity of HPLC test analysis 3- amino -4- cetyl chlorobenzoate is 98.20%.Experimental product 3- twice
Amino -4- cetyl chlorobenzoate gross mass is 489g, and testing total recovery twice is 79.67%.
Embodiment 2: be equipped with thermometer, water segregator, stirring rod three-necked flask in be separately added into 156g (0.91mol)
3- amino -4- chlorobenzoic acid, 264g (1.09mol) positive hexadecanol, 45g toluene, 182g dimethylbenzene, are heated with stirring to 50 DEG C, perseverance
18.8g (0.109mol) p-methyl benzenesulfonic acid is added in warm 1h after positive hexadecanol is completely dissolved, and continues heating in reflux temperature 152
10h is reacted at~164 DEG C, stops reaction, the methanol of 1500mL is added, and is cooled to 20 DEG C, crystallization time 5h, filtering, by filter cake
292g crude product is obtained after drying, is collected into 1500mL first time filtrate.1500mL methanol is added in crude product, is heated to 70 DEG C
Wait be completely dissolved, 10 DEG C are cooled to, recrystallizes time 8h, filtering obtains 284g finished product 3- amino -4- chlorobenzene after drying filter cake
Formic acid hexadecyl ester, yield 78.81% are collected into second of filtrate of 1500mL.HPLC test analysis 3- amino -4- chlorobenzoic acid ten
The purity of six esters is 98.50%.
2. and 3. first time filtrate and second of filtrate (about 3000mL) that step is collected is concentrated by vacuum distillation
80mL is added 1500mL distilled water crystallisation by cooling, removes catalyst after filtering, and regenerant is obtained after filter cake is dried, and 118g is added
(0.69mol) 3- amino -4- chlorobenzoic acid and 166g (0.69mol) positive hexadecanol, 45g toluene, 182g dimethylbenzene, agitating and heating
To 50 DEG C, constant temperature 0.5h, addition 18.8g (0.109mol) p-methyl benzenesulfonic acid continues to heat and return after positive hexadecanol is completely dissolved
10h is reacted at 152~164 DEG C of temperature of stream, stops reaction, the methanol of 1500mL is added, is cooled to 20 DEG C, crystallization time 5h, mistake
Filter, obtains 254g crude product after filter cake is dried.800mL isopropanol is added in crude product and is heated to 75 DEG C wait be completely dissolved, it is cold
But to 5 DEG C, time 6h is recrystallized, filtering obtains 239g finished product 3- amino -4- cetyl chlorobenzoate after drying filter cake, receive
Rate 75.76%.The purity of HPLC test analysis 3- amino -4- cetyl chlorobenzoate is 98.20%.Experimental product 3- ammonia twice
Base -4- cetyl chlorobenzoate gross mass is 523g, and testing total recovery twice is 82.54%.
Embodiment 3: be equipped with thermometer, water segregator, stirring rod three-necked flask in be separately added into 175g (1.02mol)
3- amino -4- chlorobenzoic acid, 247g (1.02mol) positive hexadecanol, 31g toluene, 275g dimethylbenzene, are heated with stirring to 50 DEG C, perseverance
The p-methyl benzenesulfonic acid of 15.6g (0.091mol) is added in warm 1h after positive hexadecanol is completely dissolved, and continues heating in reflux temperature
11h is reacted at 145~152 DEG C, stops reaction, the methanol of 1500mL is added, is cooled to 20 DEG C, crystallization time 5h, and filtering will filter
256g crude product is obtained after cake drying, is collected into 1500mL first time filtrate.1500mL methanol is added in crude product, is heated to 70
DEG C wait be completely dissolved, 5 DEG C are cooled to, recrystallizes time 6h, filtering obtains 248g finished product 3- amino -4- chlorine after drying filter cake
Benzoic acid hexadecyl ester, yield 61.40% are collected into second of filtrate of 1500mL.HPLC test analysis 3- amino -4- chlorobenzoic acid
The purity of hexadecyl ester is 98.53%.
2. and 3. first time filtrate and second of filtrate (about 3000mL) that step is collected is concentrated by vacuum distillation
80mL is added 1500mL distilled water crystallisation by cooling, removes catalyst after filtering, and regenerant is obtained after filter cake is dried, and 103g is added
(0.60mol) 3- amino -4- chlorobenzoic acid, 167g (0.60mol) positive hexadecanol, 57g toluene, 170g dimethylbenzene, agitating and heating
To 50 DEG C, constant temperature 0.5h, the p-methyl benzenesulfonic acid of 15.6g (0.091mol) is added after positive hexadecanol is completely dissolved, continues to heat
11h is reacted at 145~152 DEG C of reflux temperature, stops reaction, the methanol of 1500mL is added, is cooled to 20 DEG C, crystallization time
5h, filtering, obtains 217g crude product after filter cake is dried.800mL isopropanol is added in crude product and is heated to 75 DEG C to completely molten
Solution is cooled to 5 DEG C, recrystallizes time 6h, and filtering obtains 202g finished product 3- amino -4- chlorobenzoic acid 16 after drying filter cake
Ester, yield 54.34%.The purity of HPLC test analysis 3- amino -4- cetyl chlorobenzoate is 98.20%.Experiment produces twice
Object 3- amino -4- cetyl chlorobenzoate gross mass is 450g, and testing total recovery twice is 70.15%.
Embodiment 4: be equipped with thermometer, water segregator, stirring rod three-necked flask in be separately added into 156g (0.91mol)
3- amino -4- chlorobenzoic acid, 264g (1.09mol) positive hexadecanol, 102g toluene, 102g dimethylbenzene, are heated with stirring to 50 DEG C, perseverance
The p-methyl benzenesulfonic acid of 15.6g (0.091mol) is added in warm 1h after positive hexadecanol is completely dissolved, and continues heating in reflux temperature
12h is reacted at 144~156 DEG C, the methanol of 1500mL is added, is cooled to 20 DEG C, crystallization time 5h is obtained by filtration 270g and slightly produces
Object is collected into 1500mL first time filtrate.1500mL methanol is added in crude product, is heated to 70 DEG C wait be completely dissolved, is cooled to
10 DEG C, crystallization time 8h, filtering will obtain 262g finished product 3- amino -4- cetyl chlorobenzoate after filter cake, yield 72.71%,
It is collected into second of filtrate of 1500mL.The purity of HPLC test analysis 3- amino -4- cetyl chlorobenzoate is 98.50%.
2. and 3. first time filtrate and second of filtrate (about 3000mL) that step is collected is concentrated by vacuum distillation
80mL is added 1500mL distilled water crystallisation by cooling, removes catalyst after filtering, and regenerant is obtained after filter cake is dried, and 108g is added
(0.63mol) 3- amino -4- chlorobenzoic acid, 154g (0.63mol) positive hexadecanol, 102g toluene, 102g dimethylbenzene, agitating and heating
To 50 DEG C, constant temperature 1h, the p-methyl benzenesulfonic acid of 15.6g (0.091mol) is added after positive hexadecanol is completely dissolved, continues heating and exists
12h is reacted at 144~156 DEG C of reflux temperature, stops reaction, the methanol of 1500mL is added, is cooled to 20 DEG C, crystallization time 5h,
Filtering, obtains 250g crude product after filter cake is dried.800mL isopropanol is added in crude product and is heated to 75 DEG C wait be completely dissolved,
5 DEG C are cooled to, time 6h is recrystallized, filtering obtains 235g finished product 3- amino -4- cetyl chlorobenzoate after drying filter cake,
Yield 70.00%.The purity of HPLC test analysis 3- amino -4- cetyl chlorobenzoate is 98.30%.Experimental product 3- twice
Amino -4- cetyl chlorobenzoate gross mass is 497g, and testing total recovery twice is 81.50%.
Unaccomplished matter of the present invention is well-known technique.
Claims (4)
1. a kind of preparation method of 3- amino -4- cetyl chlorobenzoate, it is characterized in that this method comprises the following steps:
3- amino -4- chlorobenzoic acid and positive hexadecanol are added in water entrainer, are heated to 50oC, 0.5 ~ 1 h of constant temperature, then plus
Enter catalyst p-methyl benzenesulfonic acid, continues to be heated to 140 ~ 170oC reacts 6 ~ 12 h at reflux, stops heating；
Wherein, water entrainer is toluene/xylene mixture solvent, and the mass fraction of toluene is the 10%~50% of mixed solvent；N is (just
Hexadecanol): n (3- amino -4- cetyl chlorobenzoate)=1.0~1.2:1；Water entrainer quality is 3- amino -4- chlorobenzoic acid matter
1.0~2.5 times of amount；Catalyst p-methyl benzenesulfonic acid and 3- amino -4- chlorobenzoic acid molar ratio are 0.06~0.12:1；
Organic solvent is added in the reaction solution obtained one step up, then crystallisation by cooling, washing, filtering, after filter cake is dried
To crude product；Filtrate is collected；
Wherein, organic solvent is methanol, and dosage is 5~10 times of water entrainer quality；
Organic solvent is added into crude product, dissolves by heating, crystallisation by cooling, filtering obtains finished product 3- ammonia after drying filter cake
Base -4- cetyl chlorobenzoate；Filtrate is collected；
The organic solvent is methanol, and dosage is 5~10 times of water entrainer quality.
2. the preparation method of 3- amino -4- cetyl chlorobenzoate as described in claim 1, it is characterized in that this method further includes
Following steps:
By stepWithIn filtrate decompression be concentrated into 0.02~0.05 times of original filtrate volume；It is added in concentrate
Distilled water, crystallisation by cooling, filtering removal catalyst obtain regenerant after drying filter cake；It include unreacting material in regenerant
And portion of product；
The dosage of the distilled water is 5~10 times of water entrainer dosage；
Regenerant, 3- amino -4- chlorobenzoic acid and positive hexadecanol are added in water entrainer, are heated to 50oC, constant temperature 0.5 ~ 1
H adds catalyst p-methyl benzenesulfonic acid, continues to be heated to 140 ~ 170oC reacts 6 ~ 12 h at reflux, stops adding
Heat；
Water entrainer, catalyst and the stepIn composition it is identical with dosage；3- amino -4- the chlorobenzoic acid that is newly added and
Positive hexadecanol gross mass is stepObtain the quality of finished product 3- amino -4- cetyl chlorobenzoate, and n (positive hexadecanol): n
(3- amino -4- cetyl chlorobenzoate)=1.0:1；
Organic solvent is added after esterification, then crystallisation by cooling, washing, filtering, filter cake is dried after slightly produced
Object；
Organic solvent is added into crude product, dissolves by heating, crystallisation by cooling, filtering；Finished product 3- ammonia is obtained after filter cake is dried
Base -4- cetyl chlorobenzoate, filtrate are collected.
3. the preparation method of 3- amino -4- cetyl chlorobenzoate as described in claim 1 as claimed in claim 2,
Feature is stepThe organic solvent of middle recrystallization purification is methanol, and dosage is 5~10 times of water entrainer quality.
4. the preparation method of 3- amino -4- cetyl chlorobenzoate as described in claim 1 as claimed in claim 2,
Feature is stepThe organic solvent that middle filtrate recycling obtains crude product recrystallization purification with reuse is isopropanol, dosage
It is 3~8 times of water entrainer quality.
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| CN114057591A (en) * | 2022-01-14 | 2022-02-18 | 苏州开元民生科技股份有限公司 | Synthesis method of high-purity 3-amino-4-chlorobenzoic acid cetyl ester |
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Application publication date: 20190830 |