CN105367436A - Preparation method of N,N-dimethyl benzoate composite - Google Patents
Preparation method of N,N-dimethyl benzoate composite Download PDFInfo
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Abstract
The invention relates to a preparation method of an N,N-dimethyl benzoate composite, in particular to a preparation method for preparing N,N-dimethyl benzoate by using N,N-dimethylaniline, bi(trichloromethyl)carbonic ester and alcohol as raw materials. The raw materials are cheap and easy to obtain, the yield is high, a midbody does not need to be purified, a continuous reaction can be performed without replacing solvents, the preparation method is cheap, environmentally friendly, easy to implement and suitable for industrialization, and the method can be used for preparing the important chemical and medical midbody through N,N-dimethyl benzoyl chloride.
Description
Technical field
The present invention relates to a kind of N, the preparation method of N-mesitylenic acid ester compound, be specifically related to N, accelerine, two (trichloromethyl) carbonic ether and alcohol are that N prepared by raw material, the preparation method of N-mesitylenic acid ester, present method cheaper starting materials is easy to get, yield is high, and intermediate does not need to purify, not needing to change solvent can successive reaction, is the preparation method of a kind of cheapness, environmental protection, easy to operate, suitability for industrialized.And utilize present method to prepare N, the chemical industry that N-dimethyl benzoyl chloride is important and medicine intermediate.
Background technology
Dimethylaminobenzoic acid ester compound is the organism that a class has extensive use, is conventional organic bases, phase-transfer catalyst, amine promoter, sterilant, sanitas, sun-screening agent, fine-chemical intermediate, medicine intermediate etc.P-(dimethylamino)-benzoic acid ester compound is the efficient amine promoter of a class, same free radical (II) type light trigger uses together, and ultraviolet light polymerization is carried out in the aspect such as varnish colour system, ink, tackiness agent being widely used in paper, timber, metal and frosting; Ultraviolet radiation polyreaction that is single or various of monomer can also be used for, but also be good sensitizing agent, normal and other light trigger conbined usage, as: thioxanthones, acetophenones light trigger, can photoinitiation be promoted, effectively can eliminate again the interference effect that oxygen is polymerized light trigger.This series compound has a large amount in variety at present, as: (dimethylamino)-ethyl benzoate (EBD), EHA (EHA, commodity by name 507), IADB (DMBI), p-(dimethylamino)-benzoic acid methyl esters, p-(dimethylamino)-benzoic acid propyl ester, the positive butyl ester of p-(dimethylamino)-benzoic acid etc., 2-dimethyl ethyl aminobenzoate.
P-(dimethylamino)-benzoic acid ester series compound is a kind of good UVB district UV light absorber, can also as excellent uvioresistant additive, be widely used in water-fast sun care preparations, wherein EHA is classified as the sun-screening agent of first kind recommendation by U.S. FDA.Meanwhile, p-(dimethylamino)-benzoic acid ester series compound also can use as sanitas, and p-(dimethylamino)-benzoic acid methyl esters, p-(dimethylamino)-benzoic acid propyl ester, the positive butyl ester of p-(dimethylamino)-benzoic acid and solution thereof all have preservative activity.
Existing p-(dimethylamino)-benzoic acid ester series compound preparation method has three kinds:
1), p-(dimethylamino)-benzoic acid directly carries out esterification, generally makees catalyzer (BioorganicandMedicinalChemistry, 18(22) with acid: 7836-7841; 2010) esterification is carried out with correspondent alcohol;
2), P aminobenzoates carries out nitrogen and methylates, methylated reagent is generally methyl-sulfate (JournaloftheChemicalSociety, ChemicalCommunications, 17:1202-1203,1985), formaldehyde sodium cyanoborohydride (JournaloftheAmericanChemicalSociety, 120(2): 5193 – 5202,1998), methyl iodide (JournalofOrganicChemistry, 75(5): 1378-1385,2010);
3) be, with paradimethy laminobenzaldehyde raw material, catalyst oxidation silver or Silver Nitrate (Huaihai Institute of Technology journal (natural science edition), 14(2): 53-55,2005) effect under be oxidized to p-(dimethylamino)-benzoic acid, then esterification under acid catalysis.Or (TetrahedronLetters under tetrakis triphenylphosphine palladium and benzyl bromine co-catalysis, 52(41): 5319-5322,2011) or 1,2-dimethyl indazole-3-formate (OrganicLetters, 9(18): 3515-3518,2007) obtained p-(dimethylamino)-benzoic acid ester is reacted under catalysis with correspondent alcohol.
Method 1) Problems existing is that the yield of esterification is low, cause production cost higher, but also produce a large amount of acid waste water, environment is unfriendly; Method 2) shortcoming be that nitrogen methylates and is difficult to completely, methyl-sulfate toxicity is comparatively large, and waste water is many, and methyl iodide, the large cost of sodium cyanoborohydride toxicity are high; Method 3) namely avoid the reagent that use toxicity is larger, also acid waste water can not be produced, but be the use of the high precious metal chemical complex of price, tetrakis triphenylphosphine palladium and benzyl bromine catalyst or indazole salt catalyst, catalyzer cost is high and consumption is large, therefore cause whole cost very high, be not suitable for suitability for industrialized production.
2-dimethyl ethyl aminobenzoate not only can be used in photocuring system, and simultaneously or important chemical intermediate and medicine intermediate, it is less that its preparation method is reported at present.Dimethylamino Benzoyl chloride is also very important fine-chemical intermediate and medicine intermediate.The preparation method of dimethylamino Benzoyl chloride is generally be raw material by dimethylaminobenzoic acid, by preparing with highly acid oxalyl chloride, thionyl chloride, phosgene, phosphorus pentachloride back flow reaction, this class methods raw materials cost is high, requires high to reactor, and have acid gas to produce, unfavorable to environment.
Summary of the invention
The object of the invention is to overcome the shortcoming existing for existing preparation method, provide that a kind of cheaper starting materials is easy to get, use safety, reaction conditions gentleness are easy to operate and reach the preparation method of high purity, high yield, few, the eco-friendly dimethylaminobenzoic acid ester compound of the three wastes.The method is with DMA, two (trichloromethyl) carbonic ether and alcohol for raw material, and after DMA and two (trichloromethyl) carbonate reaction, the intermediate obtained carries out alcoholysis; Or obtain dimethylamino Benzoyl chloride intermediate through process later after dimethylamino-aniline and two (trichloromethyl) carbonate reaction, and then carry out alcoholysis and obtain dimethylaminobenzoic acid ester compound.Technique provided by the invention is simple, processing ease, and cost is low, and yield is high, product purity is high, no matter solid product or product liquid, and outward appearance is better, environmentally friendly, meet the requirement of environmental protection, there is significant Social benefit and economic benefit, be applicable to suitability for industrialized production.
In order to achieve the above object, the preparation method of dimethylaminobenzoic acid ester compound provided by the invention take DMA as raw material.Dimethylaminobenzoic acid ester compound and as follows with the structural formula of DMA:
Wherein, R represents the alkyl of 1-8 carbon atom.
Its synthesis step is:
Wherein, R represents the alkyl of 1-8 carbon atom.
One provided by the invention prepares dimethylamino Benzoyl chloride (formula III):
By DMA (formula II), under presence or absence organic solvent, prepare with two (trichloromethyl) carbonate reaction.
One provided by the invention prepares dimethylaminobenzoic acid ester compound (formula I):
Wherein, R represents the alkyl of 1-8 carbon atom.
1) by DMA (formula II), under presence or absence organic solvent, with two (trichloromethyl) carbonate reaction; With
2) react with alcohol subsequently;
The method need not isolation of intermediate products dimethylamino Benzoyl chloride.
One provided by the invention prepares the concrete steps of dimethylamino Benzoyl chloride (formula III):
1), by DMA be dissolved in solvent, slowly drip two (trichloromethyl) carbonic ether wherein, drip and finish, slowly heat up, rise to certain temperature, insulation reaction;
2), reaction terminate after, reaction solution carries out vacuum distillation recovered solvent, excessive raw material, rectification under vacuum or recrystallization refined product.
One provided by the invention prepares dimethylaminobenzoic acid ester compound (formula I) concrete steps:
1), by DMA be dissolved in solvent, slowly drip two (trichloromethyl) carbonic ether wherein, drip and finish, slowly heat up, rise to certain temperature, insulation reaction;
2), react completely after, drip alcohol, drip finish, insulation reaction;
3), after reaction terminates, reaction solution is slowly added drop-wise in water, after hydrolysis fully, stratification, organic phase saturated common salt water washing;
4), the solution after washing is carried out vacuum distillation recovered solvent, excessive raw material, rectification under vacuum or recrystallization refined product.
The preparation method of dimethylaminobenzoic acid ester compound provided by the invention or dimethylamino Benzoyl chloride, is characterized in that the ratio of DMA described in step 1) and two (trichloromethyl) carbonic ether amount of substance is selected from 4-15:1.
The preparation method of dimethylaminobenzoic acid ester compound provided by the invention or dimethylamino Benzoyl chloride, is characterized in that solvent described in step 1) is selected from chlorobenzene, toluene, ethylene dichloride, benzene, methylene dichloride.
The preparation method of dimethylaminobenzoic acid ester compound provided by the invention or dimethylamino Benzoyl chloride, is characterized in that step 1) degree of intensification is selected from 40-80 DEG C.
The preparation method of dimethylaminobenzoic acid ester compound provided by the invention, is characterized in that step 2) described in temperature of reaction be selected from-20-60 DEG C.
The present invention prepares dimethylaminobenzoic acid ester compound alcohol used and is selected from alcohol containing 1-8 carbon atom, comprise the alcohol of straight chain and straight chain, such as: methyl alcohol, ethanol, propyl alcohol, butanols, Pentyl alcohol, primary isoamyl alcohol, neopentyl alcohol, n-hexyl alcohol, 2-hexanol, 3-hexanol, 3-methyl-1-pentene alcohol, 3-methyl-2-amylalcohol, 3-methyl-3-amylalcohol, normal heptane, positive isooctyl alcohol etc.
Dimethylaminobenzoic acid ester compound prepared by the present invention is 2-dimethylaminobenzoic acid ester compound and 4-dimethylaminobenzoic acid ester compound.Dimethylamino Benzoyl chloride prepared by the present invention is 2-dimethylamino Benzoyl chloride and 4-dimethylamino Benzoyl chloride.
Dimethylaminobenzoic acid ester compound prepared by the present invention and dimethylamino Benzoyl chloride can regulate reaction conditions (such as temperature of reaction, reaction times) to obtain based on the dimethylaminobenzoic acid ester compound of 2-position or 4-position product and dimethylamino Benzoyl chloride product, and 2-position and 4-position product can carry out separating-purifying by rectification under vacuum or recrystallization.
The preparation method of dimethylamino Benzoyl chloride provided by the invention be with DMA and two (trichloromethyl) carbonic ether for raw material, be obtained by reacting under the reaction conditions of gentleness, purify and obtain dimethylamino Benzoyl chloride product; The preparation of dimethylaminobenzoic acid ester compound is that raw material reacts with DMA and two (trichloromethyl) carbonic ether, after reacting completely, do not need to purify to intermediate, directly and alcohol react, obtain product through aftertreatment.The cheaper starting materials that this preparation method uses is easy to get and safety, and the gentle easily control of reaction conditions, the preparation process of dimethylaminobenzoic acid ester compound does not need to purify to intermediate, can successive reaction.Dangerous little in operating process, operate fairly simple, after reaction terminates, reaction solution obtains qualified product through distillation, rectifying or recrystallization.The method is environmental friendliness not only, and can reduce production cost.
Specific embodiment
In order to be illustrated more clearly in the present invention, nonlimiting examples is hereinafter taked to be described further.
Embodiment 1: to the preparation of dimethylamino Benzoyl chloride
In the four-hole bottle of 500ml, add N, accelerine (72.7g, 0.6mol) with 30ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 60ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 65 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, be down to room temperature, after first normal pressure, chlorobenzene is reclaimed in underpressure distillation, chlorobenzene has reclaimed, reclaim excess raw material N, accelerine, last rectification under vacuum obtains product 33.1g (collecting the condition of cut: 175 ~ 180 DEG C/15mmHg), yield 60%, purity 99.0%.
Embodiment 2: to the preparation of dimethylamino Benzoyl chloride
In the four-hole bottle of 500ml, add N, accelerine (121.2g, 1.0mol) with 60ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 120ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 65 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, be down to room temperature, after first normal pressure, chlorobenzene is reclaimed in underpressure distillation, chlorobenzene has reclaimed, reclaim excess raw material N, accelerine, last rectification under vacuum obtains product 44.1g (collecting the condition of cut: 175 ~ 180 DEG C/15mmHg), yield 80%, purity 99.1%.
Embodiment 3: the preparation of adjacent dimethylamino Benzoyl chloride
In the four-hole bottle of 500ml, add N, accelerine (121.2g, 1.0mol) with 60ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 120ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 40 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, adjacent dimethylamino Benzoyl chloride in gas-chromatography display reaction solution: be 75:25 to dimethylamino Benzoyl chloride, solvent and excess raw material are reclaimed, to purify adjacent dimethylamino Benzoyl chloride by rectification under vacuum.
Embodiment 4: the preparation of p-(dimethylamino)-benzoic acid methyl esters
In the four-hole bottle of 500ml, add N, accelerine (121.2g, 1.0mol) with 60ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 120ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 65 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, be down to temperature to 30 DEG C, slow dropping 12.8g anhydrous methanol, drip and finish, insulation reaction, TLC or GC monitors reaction, after reaction terminates, slowly reaction solution is put in 150ml water, stir hydrolysis, and control temperature is at about 25 DEG C, after 1h, stratification, organic phase saturated common salt water washing, with anhydrous sodium sulfate drying, vacuum distillation recovered solvent and excess raw material, carry out rectification under vacuum purification p-(dimethylamino)-benzoic acid methyl esters 43.0g (collecting the condition of cut: 101 ~ 105 DEG C/0.05mmHg) again, yield 80%, purity 99.2%.
Embodiment 5: the preparation of (dimethylamino)-ethyl benzoate
In the four-hole bottle of 500ml, add N, accelerine (121.2g, 1.0mol) with 60ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 120ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 65 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, be down to temperature to 30 DEG C, slow dropping 18.4g dehydrated alcohol, drip and finish, insulation reaction, TLC or GC monitors reaction, after reaction terminates, slowly reaction solution is put in 150ml water, stir hydrolysis, and control temperature is at about 25 DEG C, after 1h, stratification, organic phase saturated common salt water washing, with anhydrous sodium sulfate drying, vacuum distillation recovered solvent and excess raw material, carry out rectification under vacuum purification (dimethylamino)-ethyl benzoate 47.2g (collecting the condition of cut: 110 ~ 115 DEG C/0.02mmHg) again, yield 81%, purity 99.3%.
Embodiment 6: the preparation of IADB
In the four-hole bottle of 500ml, add N, accelerine (121.2g, 1.0mol) with 60ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 120ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 60 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, be down to temperature to 30 DEG C, slow dropping 35.3g primary isoamyl alcohol, drip and finish, insulation reaction, TLC or GC monitors reaction, after reaction terminates, slowly reaction solution is put in 150ml water, stir hydrolysis, and control temperature is at about 25 DEG C, after 1h, stratification, organic phase saturated common salt water washing, with anhydrous sodium sulfate drying, vacuum distillation recovered solvent and excess raw material, carry out rectification under vacuum purification IADB 55.8g (collecting the condition of cut: 150 ~ 155 DEG C/2.5mmHg) again, yield 79%, purity 99.5%.
Embodiment 7: the preparation of EHA
In the four-hole bottle of 500ml, add N, accelerine (121.2g, 1.0mol) with 60ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 120ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 60 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, be down to temperature to 30 DEG C, slow dropping 35.3g primary isoamyl alcohol, drip and finish, insulation reaction, TLC or GC monitors reaction, after reaction terminates, slowly reaction solution is put in 150ml water, stir hydrolysis, and control temperature is at about 25 DEG C, after 1h, stratification, organic phase saturated common salt water washing, with anhydrous sodium sulfate drying, vacuum distillation recovered solvent and excess raw material, carry out rectification under vacuum purification IADB 62.4g (collecting the condition of cut: 200 ~ 205 DEG C/3mmHg) again, yield 75%, purity 99.8%.
Embodiment 8: the preparation of adjacent dimethyl ethyl aminobenzoate
In the four-hole bottle of 500ml, add N, accelerine (121.2g, 1.0mol) with 60ml chlorobenzene, stir, by two (trichloromethyl) carbonic ether (29.7g, 0.1mol) be dissolved in 120ml chlorobenzene, slowly be added drop-wise to N, in the chlorobenzene solution of accelerine, 2h drips complete, then 40 DEG C are slowly warming up to, insulation reaction, TLC or GC monitors reaction, after reacting completely, be down to temperature to 30 DEG C, slow dropping 18.4g dehydrated alcohol, drip and finish, insulation reaction, TLC or GC monitors reaction, after reaction terminates, slowly reaction solution is put in 150ml water, stir hydrolysis, and control temperature is at about 25 DEG C, after 1h, stratification, organic phase saturated common salt water washing, with anhydrous sodium sulfate drying, adjacent dimethyl ethyl aminobenzoate in gas-chromatography display organic phase: (dimethylamino)-ethyl benzoate is 77:23, vacuum distillation recovered solvent and excess raw material, carry out rectification under vacuum again to purify adjacent dimethylaminobenzoic acid different ethyl ester ester 34.9g (collecting the condition of cut: 125 ~ 130 DEG C/3mmHg), yield 60%, purity 98.8%.
Claims (8)
1. the preparation method of a dimethylaminobenzoic acid ester compound (formula I):
Wherein, R represents the alkyl of 1-8 carbon atom;
1) by DMA, under presence or absence organic solvent, with two (trichloromethyl) carbonate reaction; With
2) react with alcohol subsequently;
The method need not isolation of intermediate products dimethylamino Benzoyl chloride.
2. the preparation method of a dimethylamino Benzoyl chloride (formula III):
By DMA, under presence or absence organic solvent, prepare with two (trichloromethyl) carbonate reaction.
3. the preparation method of dimethylaminobenzoic acid ester compound according to claim 1, is characterized in that the concrete steps comprised:
1), by DMA be dissolved in solvent, slowly drip two (trichloromethyl) carbonic ether wherein, drip and finish, slowly heat up, rise to certain temperature, insulation reaction;
2), react completely after, drip alcohol, drip finish, insulation reaction;
3), reaction terminate after, under stirring, reaction solution is slowly added drop-wise in water, then stratification, organic phase saturated common salt water washing;
4), the solution after washing is carried out vacuum distillation recovered solvent, excessive raw material, rectification under vacuum or recrystallization refined product.
4. the preparation method of dimethylamino Benzoyl chloride according to claim 2, is characterized in that the concrete steps comprised:
1), by DMA be dissolved in solvent, slowly drip two (trichloromethyl) carbonic ether wherein, drip and finish, slowly heat up, rise to certain temperature, insulation reaction;
2), reaction terminate after, reaction solution carries out vacuum distillation recovered solvent, excessive raw material, rectification under vacuum or recrystallization refined product.
5. the preparation method according to claim 3 and 4, is characterized in that the ratio of DMA described in step 1) and two (trichloromethyl) carbonic ether amount of substance is selected from 4-15:1.
6. the preparation method according to claim 3 and 4, is characterized in that solvent described in step 1) is selected from chlorobenzene, toluene, ethylene dichloride, benzene, methylene dichloride.
7. the preparation method according to claim 3 and 4, is characterized in that step 1) degree of intensification is selected from 40-80 DEG C.
8. preparation method according to claim 3, is characterized in that step 2) described in temperature of reaction be selected from-20-60 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107935817A (en) * | 2017-12-12 | 2018-04-20 | 浙江优创材料科技股份有限公司 | Isooctyl p-dimethylaminobenzoate crude product recycles the devices and methods therefor of isooctanol |
| CN112707830A (en) * | 2020-12-28 | 2021-04-27 | 天津久日新材料股份有限公司 | Method for preparing tetraethyl mikrolon |
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| US2882472A (en) * | 1955-11-02 | 1959-04-14 | Sprague Electric Co | Electrical capacitors |
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| 季宝等: ""三光气的反应机理和应用"", 《科技情报开发与经济》 * |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935817A (en) * | 2017-12-12 | 2018-04-20 | 浙江优创材料科技股份有限公司 | Isooctyl p-dimethylaminobenzoate crude product recycles the devices and methods therefor of isooctanol |
| CN107935817B (en) * | 2017-12-12 | 2023-08-29 | 浙江优创材料科技股份有限公司 | Device and method for recovering isooctyl alcohol from isooctyl p-dimethylaminobenzoate crude product |
| CN112707830A (en) * | 2020-12-28 | 2021-04-27 | 天津久日新材料股份有限公司 | Method for preparing tetraethyl mikrolon |
| CN112707830B (en) * | 2020-12-28 | 2023-09-29 | 天津久日新材料股份有限公司 | Preparation method of tetraethyl ketone |
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