CN106008237B - Double Diethylaminoethanol ester citrate compounds of plant growth regulator terephthalic acid (TPA) and preparation method thereof - Google Patents
Double Diethylaminoethanol ester citrate compounds of plant growth regulator terephthalic acid (TPA) and preparation method thereof Download PDFInfo
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- CN106008237B CN106008237B CN201610349802.2A CN201610349802A CN106008237B CN 106008237 B CN106008237 B CN 106008237B CN 201610349802 A CN201610349802 A CN 201610349802A CN 106008237 B CN106008237 B CN 106008237B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/14—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Abstract
The present invention relates to double Diethylaminoethanol ester citrate compounds of a kind of new plant growth regulator terephthalic acid (TPA) and preparation method thereof, the structure of the compound is shown below：
Description
Technical field
The present invention relates to the double Diethylaminoethanol ester citrate compounds of a plant growth regulators terephthalic acid (TPA)
And preparation method thereof.The compound has improvement seed enzymatic activity, promotes cell division, promotes seed to sprout, promotes plant to give birth to
Long, enhancing photosynthesis, crop yield is improved, improve fruit quality and strengthens the purposes such as plant stress-resistance.
Background technology
The mankind will face lot of challenges in 2l centuries, wherein most primary is exactly population and food problem.Grain is to the mankind
The survival and development have great importance, and a data of FAO (Food and Agriculture Organization of the United Nation) shows, world agriculture faces annual increase by 700
The immense pressure of ten thousand populations, and it is limited to plough.A data of China National Bureau of Statistics of China shows that continent population increases every year
Add 15,000,000 people or so, to 2015 oneself up to 1,400,000,000 or so.Existing 1,400,000,000 mu of the arable land of China, accounts for the 7% of the world, and population accounts for generation
The 25% of boundary, this situation is quite severe, thus effectively improve existing arable land quality and unit area yield turn into work as
Business is anxious.In this respect, in addition to cultivating fine seed strains and rationally cultivating, an effective solution is exactly biological living using having
Property organic substance, by adjusting the growth of plant, reach increase yield and improve quality purpose.
Inventor by market by applying more DCPTA N, N- diethyl -2- at present（3,4- dichlorophenoxies）Second
Amine (DCPTA) and caproic acid Diethylaminoethanol ester（DA-6）Inspiration, will have diethylamino ethoxy group in both structures
Split is carried out with terephthalic acid (TPA), that is, obtains the compound with bioactivity containing pair diethylamino ethoxy structures-right
The double Diethylaminoethanol esters of phthalic acid.It is polyfunctional group synergistic structure, contains two diethylamino ethoxies in molecule, makes it
With more excellent plant growth regulation.
The content of the invention
An object of the present invention is to propose a kind of double diethylamine of compound-terephthalic acid (TPA) with bioactivity
Base ethanol ester citrate.The compound have it is simple in construction, it is soluble in water, easily by cell membrane enter cell body in.With showing
Some plant growth regulator compare, significant effect few with amount of application, and low toxicity is environmentally safe, while have mould proof anti-
The advantages that bacterium, deficiency of the prior art can be overcome.
For achieving the above object, present invention employs following technical scheme：
A kind of double Diethylaminoethanol ester citrate compounds of terephthalic acid (TPA), it is characterised in that the knot of the compound
Structure is shown below：
It is another object of the present invention to propose a kind of preparation side of the double Diethylaminoethanol ester citrates of terephthalic acid (TPA)
Method.Its technique is simple, is easy to large-scale production, and raw material is cheap and easy to get, and equipment investment is few, and cost is cheap, and atom utilization is high,
Environmental pollution is small, and this method is：
A certain amount of organic solvent, proper catalyst are added in the reactor equipped with water knockout drum and reflux, then is added
Enter the terephthalic acid (TPA) and N, N- diethylaminoethanol of certain mol proportion, stir lower heating, in 110 DEG C~150 DEG C temperature next time
Flow point water reacts, and 5~10h is reacted, until the water separated reaches theoretical amount, Filtration of catalyst（Recovery uses）, filtrate decompression
Distill out organic solvent（Recovery uses）, excessive diethylaminoethanol（Recovery uses）And low boilers, bottoms addition pair
The double Diethylaminoethanol ester Theoretical Mass 5%-10% activated decolorations of phthalic acid, stir 30 minutes, filter to obtain faint yellow oil
The double Diethylaminoethanol esters of shape liquid terephthalic acid (TPA).Again by the double Diethylaminoethanol esters of terephthalic acid (TPA) and twice mole of lemon
Lemon acid is put into reactor, is heated with stirring to 120 DEG C, after citric acid melts, and stirs lower crystallisation by cooling into salt, that is, it is solid to obtain white
The double Diethylaminoethanol ester citrates of body product terephthalic acid.
A certain amount of organic solvent as described above is dimethylbenzene or toluene, and its dosage volume milliliter number is terephthalic acid (TPA) matter
Measure grams 1-8 times.
The terephthalic acid (TPA) and N, N- diethylaminoethanol of certain mol proportion as described above are terephthalic acid (TPA):N, N- bis-
The mol ratio of ethylaminoethanol is 1:2-1:3.
Proper catalyst as described above is titanyl sulfate, titanium dioxide or silica gel, and its dosage is terephthalic acid (TPA) quality
The 2%-10% of grams.
The double Diethylaminoethanol esters of terephthalic acid (TPA) of the present invention are pale yellow oily liquid, not soluble in water, index of refraction:nD 25=
1.753 density（20℃）:0.7874g/cm3；Yield is 83.1%~90.5%, the double Diethylaminoethanol esters of terephthalic acid (TPA)
Citrate compound is white powdery solids, and fusing point is 116 DEG C, soluble in water.Plant growth regulator terephthaldehyde
The preparation principle of sour double Diethylaminoethanol ester citrates is shown below：
Compared with prior art, the present invention is advantageous in that：
（1）Contain two diethylaminoethanol ester active function groups in one molecule of structure of the present invention, with recessiveness to benzene two
Carrier, atom utilization height, active function groups superposition produce synergistic function to formic acid active body structure each other, and it can play excellent
Good plant growth regulation, significantly improve its active effect.
（2）The compounds of this invention, which has, to be promoted seed to sprout, promotes plant growth, enhancing photosynthesis, improves and make produce
Amount, improve the effect such as fruit quality and enhancing stress resistance of plant, its is widely used, is broad spectrum type active regulator.
（3）The compounds of this invention has that dosage is few, small toxicity, it is free from environmental pollution the advantages that.
（4）The compounds of this invention preparation technology used catalyst and solvent and the Diethylaminoethanol of excess are all directly to return
Receive and use, do not produce pollution, do not cause to waste, belong to green preparation process.
（5）When the compounds of this invention preparation technology silica gel makees catalyst, itself has decolorization, can save to product
Decolorization.
（6）The compounds of this invention preparation method is simple, and raw material is cheap and easy to get, and cost is low, and equipment investment is few, is easy to scale
Production, there is good application and development prospect.
Brief description of the drawings
In order to further illustrate that the structure of product and performance spy provide drawings described below.
Fig. 1 is the infrared spectrogram of the double Diethylaminoethanol esters of terephthalic acid (TPA)；Fig. 1 shows, in 1750cm-1Nearby occur
Strong absworption peak, corresponds to the stretching vibration of ester carbonyl group；In addition, 2900cm-1Nearby there is CH2The stretching vibration of middle c h bond；
1350cm-1Nearby there is the stretching vibration of C-N-C keys；1630cm-1Locate the skeleton stretching vibration peak for phenyl ring；3080cm-1Locate be
The C-H stretching vibration peaks of phenyl ring.
Fig. 2 is the nuclear magnetic spectrum figure of the double Diethylaminoethanol esters of terephthalic acid (TPA)；Fig. 2 shows, deuterochloroform is solvent, δ
8.02 ~ 8.25 be benzene ring hydrogen peak；δ 4.36 ~ 4.42 is-OCH2CH2The methylene hydrogen peak that N is connected with oxygen；δ2.80~2.88
For-OCH2CH2The methylene hydrogen peak that N is connected with nitrogen；δ 2.56 ~ 2.68 is N- (CH2CH3)2The methylene hydrogen peak being connected with nitrogen；δ
1.03 ~ 1.10 be N- (CH2CH3)2In methyl hydrogen peak.
Embodiment
Technical scheme is described further below in conjunction with specific embodiment.
Embodiment 1 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 35.1g (0.3mol) N, N- diethylaminoethanol, 0.8g titanyl sulfates, 30ml dimethylbenzene, stirring
150 DEG C of back flow reaction 5h are heated to, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate turn
In the there-necked flask for entering another 250ml, solvent is evaporated under reduced pressure out（Recovery uses）, excessive diethylaminoethanol（Recovery uses）
And after low boilers, add 3.0g atlapulgites and stir 30 minutes, be cooled to less than 80 DEG C, filter to obtain pale yellow oily liquid pair
The double Diethylaminoethanol ester 32.94g of phthalic acid, yield 90.5%.Again by the double Diethylaminoethanol esters of terephthalic acid (TPA) and twice
Mole citric acid mix and be heated to 120 DEG C, after melting citric acid, stir lower crystallisation by cooling into salt, that is, obtain white
The double Diethylaminoethanol ester citrates of pulverulent solids product terephthalic acid.Its fusing point：116℃.
Embodiment 2 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 23.4 g (0.2mol) N, N- diethylaminoethanol, 0.8g titanyl sulfates, 40ml dimethylbenzene, is stirred
Mix and be heated to 140 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate
It is transferred in another 250ml there-necked flask, is evaporated under reduced pressure out solvent（Recovery uses）And after low boilers, it is white to add 3.0g activity
Soil stirring 30 minutes, is cooled to less than 80 DEG C, filters to obtain the double Diethylaminoethanol esters of pale yellow oily liquid terephthalic acid (TPA)
30.9g, yield 84.9%.The double Diethylaminoethanol esters of terephthalic acid (TPA) and twice mole of citric acid are mixed and heated again
To 120 DEG C, after melting citric acid, lower crystallisation by cooling is stirred into salt, that is, obtains white powdery solids product terephthalic acid
Double Diethylaminoethanol ester citrates.Its fusing point：116℃.
Embodiment 3 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 35.1g (0.3mol) N, N- diethylaminoethanol, 0.8g titanium dioxide, 20ml dimethylbenzene, stirring
150 DEG C of back flow reaction 9h are heated to, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate turn
In the there-necked flask for entering another 250ml, solvent is evaporated under reduced pressure out（Recovery uses）, excessive diethylaminoethanol（Recovery uses）
And after low boilers, add 3.0g atlapulgites and stir 30 minutes, be cooled to less than 80 DEG C, filter to obtain pale yellow oily liquid pair
The double Diethylaminoethanol ester 32.47g of phthalic acid, yield 89.2%.The double Diethylaminoethanol esters of terephthalic acid (TPA) are rubbed with twice
Your citric acid mixes and is heated to 120 DEG C, after melting citric acid, stirs lower crystallisation by cooling into salt, that is, obtains white powder
The double Diethylaminoethanol ester citrates of last shape solid product terephthalic acid (TPA).Its fusing point：116℃.
Embodiment 4 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 29.3g (0.25mol) N, N- diethylaminoethanol, 0.6g titanyl sulfates, 40ml dimethylbenzene, is stirred
Mix and be heated to 140 DEG C of back flow reaction 7h, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate
It is transferred in another 250ml there-necked flask, is evaporated under reduced pressure out solvent（Recovery uses）, excessive diethylaminoethanol（Recovery makes
With）And after low boilers, add 3.0g atlapulgites and stir 30 minutes, be cooled to less than 80 DEG C, filter to obtain pale yellow oily liquid
The double Diethylaminoethanol ester 31.56g of body terephthalic acid (TPA), yield 86.7%.By the double Diethylaminoethanol esters and two of terephthalic acid (TPA)
Times mole citric acid mix and be heated to 120 DEG C, after melting citric acid, stir lower crystallisation by cooling into salt, that is, obtain white
The double Diethylaminoethanol ester citrates of the powdered solid product terephthalic acid (TPA) of color.Its fusing point：116℃.
Embodiment 5 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 29.3g (0.25mol) N, N- diethylaminoethanol, 1 g silica gel, 40ml dimethylbenzene, agitating and heating
To 140 DEG C of back flow reaction 7h, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate is transferred to separately
In one 250ml there-necked flask, solvent is evaporated under reduced pressure out（Recovery uses）, excessive diethylaminoethanol（Recovery uses）It is and low
After boiling point thing, the double Diethylaminoethanol ester 32.1g of pale yellow oily liquid terephthalic acid (TPA), yield 88.2% are obtained.Will be to benzene two
The double Diethylaminoethanol esters of formic acid and twice mole of citric acid mix and are heated to 120 DEG C, after melting citric acid, stirring
Lower crystallisation by cooling obtains the double Diethylaminoethanol ester citrates of white powdery solids product terephthalic acid into salt.Its
Fusing point：116℃.
Embodiment 6 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 35.1g (0.3mol) N, N- diethylaminoethanol, 0.7g titanyl sulfates, 30ml toluene, stirring add
Heat is to 120 DEG C of back flow reaction 6h, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate is transferred to
In another 250ml there-necked flask, solvent is evaporated under reduced pressure out（Recovery uses）, excessive diethylaminoethanol（Recovery uses）And
After low boilers, add 3.0g atlapulgites and stir 30 minutes, be cooled to less than 80 DEG C, filter pale yellow oily liquid to benzene
The double Diethylaminoethanol ester 32.36g of dioctyl phthalate, yield 88.9%.By the double Diethylaminoethanol esters of terephthalic acid (TPA) and twice mole
Citric acid mix and be heated to 120 DEG C, after melting citric acid, stir lower crystallisation by cooling into salt, that is, obtain white powder
The double Diethylaminoethanol ester citrates of shape solid product terephthalic acid (TPA).Its fusing point：116℃.
Embodiment 7 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 35.1g (0.3mol) N, N- diethylaminoethanol, 0.8g titanium dioxide, 30ml toluene, stirring add
Heat is to 120 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate is transferred to
In another 250ml there-necked flask, solvent is evaporated under reduced pressure out（Recovery uses）, excessive diethylaminoethanol（Recovery uses）And
After low boilers, add 3.0g atlapulgites and stir 30 minutes, be cooled to less than 80 DEG C, filter pale yellow oily liquid to benzene
The double Diethylaminoethanol ester 32.29g of dioctyl phthalate, yield 88.7%.By the double Diethylaminoethanol esters of terephthalic acid (TPA) and twice mole
Citric acid mix and be heated to 120 DEG C, after melting citric acid, stir lower crystallisation by cooling into salt, that is, obtain white powder
The double Diethylaminoethanol ester citrates of shape solid product terephthalic acid (TPA).Its fusing point：116℃.
Embodiment 8 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 23.4 g (0.2mol) N, N- diethylaminoethanol, 0.8g titanyl sulfates, 40ml toluene, stirring
110 DEG C of back flow reaction 8h are heated to, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate turn
In the there-necked flask for entering another 250ml, solvent is evaporated under reduced pressure out（Recovery uses）And after low boilers, add 3.0g atlapulgites
Stirring 30 minutes, is cooled to less than 80 DEG C, filters to obtain the double Diethylaminoethanol esters of pale yellow oily liquid terephthalic acid (TPA)
30.22g yield 83.1%.The double Diethylaminoethanol esters of terephthalic acid (TPA) are heated to twice mole of citric acid mixing
120 DEG C, after melting citric acid, lower crystallisation by cooling is stirred into salt, that is, it is double to obtain white powdery solids product terephthalic acid
Diethylaminoethanol ester citrate.Its fusing point：116℃.
Embodiment 9 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 29.3g (0.25mol) N, N- diethylaminoethanol, 0.8g titanyl sulfates, 40ml toluene, stirring
110 DEG C of back flow reaction 7h are heated to, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate turn
In the there-necked flask for entering another 250ml, solvent is evaporated under reduced pressure out（Recovery uses）, excessive diethylaminoethanol（Recovery uses）
And after low boilers, add 3.0g atlapulgites and stir 30 minutes, be cooled to less than 80 DEG C, filter to obtain pale yellow oily liquid pair
The double Diethylaminoethanol ester 31.30g of phthalic acid, yield 86.0%.The double Diethylaminoethanol esters of terephthalic acid (TPA) are rubbed with twice
Your citric acid mixes and is heated to 120 DEG C, after melting citric acid, stirs lower crystallisation by cooling into salt, that is, obtains white powder
The double Diethylaminoethanol ester citrates of last shape solid product terephthalic acid (TPA).Its fusing point：116℃.
Embodiment 10 adds 16.6g in the 250ml four-hole boiling flasks equipped with agitator and water knockout drum and reflux
(0.1mol) terephthalic acid (TPA), 29.3g (0.25mol) N, N- diethylaminoethanol, 1 g silica gel, 40ml toluene, is heated with stirring to
120 DEG C of back flow reaction 10h, until separating 3.6g (0.2mol) water, Filtration of catalyst（Direct reuse）, filtrate is transferred to another
In individual 250ml there-necked flask, solvent is evaporated under reduced pressure out（Recovery uses）, excessive diethylaminoethanol（Recovery uses）And low boiling
After point thing, the double Diethylaminoethanol ester 31.01g of pale yellow oily liquid terephthalic acid (TPA), yield 85.2% are obtained.Again will be to benzene
The double Diethylaminoethanol esters of dioctyl phthalate and twice mole of citric acid mix and are heated to 120 DEG C, after melting citric acid, stir
Lower crystallisation by cooling is mixed into salt, that is, obtains the double Diethylaminoethanol ester citrates of white powdery solids product terephthalic acid.
Its fusing point：116℃.
The terephthalic acid (TPA) of table 1 is that raw material prepares main technologic parameters
| Sequence number | Diethylaminoethanol | Catalyst | Solvent | Quantity of solvent | Temperature DEG C | Time | Yield % |
| 1 | 35.1g(0.3mol) | 0.8g titanyl sulfates | Dimethylbenzene | 30ml | 150 | 5h | 90.5% |
| 2 | 23.4g(0.2mol) | 0.8g titanyl sulfates | Dimethylbenzene | 40ml | 140 | 8h | 84.9% |
| 3 | 35.1g(0.3mol) | 0.8g titanium dioxide | Dimethylbenzene | 20ml | 150 | 9h | 89.2% |
| 4 | 29.3g(0.25mol) | 0.6g titanyl sulfates | Dimethylbenzene | 40ml | 140 | 7h | 86.7% |
| 5 | 29.3g(0.25mol) | 1g silica gel | Dimethylbenzene | 40ml | 140 | 7h | 88.2% |
| 6 | 35.1g(0.3mol) | 0.7g titanyl sulfates | Toluene | 30ml | 120 | 6h | 88.9% |
| 7 | 35.1g(0.3mol) | 0.8g titanium dioxide | Toluene | 30ml | 120 | 8h | 88.7% |
| 8 | 23.4g(0.2mol) | 0.8g titanyl sulfates | Toluene | 40ml | 110 | 8h | 83.1% |
| 9 | 29.3g(0.25mol) | 0.8g titanyl sulfates | Toluene | 40ml | 110 | 7h | 86.0% |
| 10 | 29.3g(0.25mol) | 1g silica gel | Toluene | 40ml | 120 | 10h | 85.2% |
Note:Terephthalic acid (TPA) inventory is 16.6g (0.1mol) in table 1
Inventor by the double Diethylaminoethanol ester citric acid hydrochlorates of the terephthalic acid (TPA) of above-mentioned preparation be used for green vegetables, soya bean,
Wheat, rape, rice paddy seed reference《International seed inspection procedure》(1985)、《Crop seeds inspection procedure》(1995) conduct
The standard (to grow 1cm as germination) whether evaluation seed germinates, has made biological activity test, method of testing is as follows:
Using plate culture, the double Diethylaminoethanol ester citrates of terephthalic acid (TPA) are configured to 100mg/L respectively,
70mg/L, 40mg/L, 10mg/L tetra- strength solutions, it is studied to green vegetables, soya bean, wheat, rape, rice seedling root system
Growth regulating acts on.Make blank test with distilled water, the DA-6 solution of same concentrations makees standard control group, uses respective concentration respectively
Solution immersion green vegetables, soya bean, wheat, rape, rice paddy seed 6h -8h, be then respectively placed in temperature for 23 DEG C, 25 DEG C, 20
DEG C, 23 DEG C, measure the length of its root system and stem after 28 DEG C of incubated rooms culture 4d -6d, and count germination number, to
Lower formula calculates germination percentage and regulation percent activity.
Germination percentage=germinative number/seed sum
A=(N-N0)/N0×100%
A-it is sample regulation activity
The length of N-cultivated in the compound solution root measured
The culture of N0-in distilled water measure with length
The number of the double Diethylaminoethanol ester citrates of terephthalic acid (TPA) prepared by the present invention to plant growth regulating activity
According to being shown in Table 2, table 3, table 4, table 5, table 6：
The double Diethylaminoethanol ester citrates of the terephthalic acid (TPA) of table 2 are used for green vegetables seed (50) Seed germination data
The double Diethylaminoethanol ester citrates of the terephthalic acid (TPA) of table 3 are used for soya bean seed (10) Seed germination data
The double Diethylaminoethanol ester citrates of the terephthalic acid (TPA) of table 4 are used for wheat seed (30) Seed germination data
The double Diethylaminoethanol ester citrates of the terephthalic acid (TPA) of table 5 are used for rape seed (50) Seed germination data
The double Diethylaminoethanol ester citrates of the terephthalic acid (TPA) of table 6 are used for rice paddy seed (30) Seed germination data
Claims (2)
1. the preparation method of the double Diethylaminoethanol ester citrate compounds of a plant growth regulators terephthalic acid (TPA), its
It is characterised by, this method is：
Organic solvent toluene or dimethylbenzene, its dosage volume milliliter number are added in the reactor equipped with water knockout drum and reflux
It is 1-8 times of terephthalic acid (TPA) quality grams, adds terephthalic acid (TPA) quality grams 2%-10% catalyst sulfuric acid oxygen titanium, then
Terephthalic acid (TPA) and N, N-diethylaminoethanol are added, controls terephthalic acid (TPA) and N, the mol ratio of N-diethylaminoethanol to exist
1: 2-1: 3, lower heating is stirred, reflux water-dividing reacts at a temperature of 110~150 DEG C, 5~10h is reacted, until separating what is generated
The water of theoretical amount, Filtration of catalyst, filtrate decompression distill out organic solvent, excessive diethylaminoethanol and low boiling
Thing, bottoms add the double Diethylaminoethanol ester Theoretical Mass 5%-10% activated decolorations of terephthalic acid (TPA), stirred 30 minutes,
Filter to obtain the double Diethylaminoethanol esters of pale yellow oily liquid terephthalic acid (TPA)；Again by the double Diethylaminoethanol esters of terephthalic acid (TPA)
Citric acid with twice mole is put into reactor, agitating and heating, after citric acid melts, is stirred lower crystallisation by cooling into salt, is produced
To the double Diethylaminoethanol ester citrates of white solid product terephthalic acid (TPA), the structure of the compound is shown below：
。
2. the double Diethylaminoethanol ester citrate chemical combination of plant growth regulators terephthalic acid (TPA) as claimed in claim 1
The preparation method of thing, it is characterised in that：Described Filtration of catalyst, filtrate decompression distill out organic solvent, excessive two
Catalyst that ethylaminoethanol is recovered to, organic solvent, diethylaminoethanol recycling.
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| CN103641781A (en) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | Application of naphthalimide type compounds and salts thereof as plant growth regulators |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641781A (en) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | Application of naphthalimide type compounds and salts thereof as plant growth regulators |
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| Evaluation of the activity of a number of procaine derivatives and analogous compounds against powdery mildew (Sphaerotheca fuliginea) on cucumber;Niemann, G. J. ET AL;《Annals of Applied Biology》;19661231;第57卷(第1期);53-58 * |
| 新型植物生长调节剂DA-6的合成与活性研究;王铭琦;《中国优秀硕士学位论文全文数据库 农业科技辑》;20070115(第1期);D046-18 * |
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