CN105906517A - Plant growth regulator decanedioic acid double diethylamine alcohol ester acetate citrate compound and preparation method thereof - Google Patents

Plant growth regulator decanedioic acid double diethylamine alcohol ester acetate citrate compound and preparation method thereof Download PDF

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CN105906517A
CN105906517A CN201610349823.4A CN201610349823A CN105906517A CN 105906517 A CN105906517 A CN 105906517A CN 201610349823 A CN201610349823 A CN 201610349823A CN 105906517 A CN105906517 A CN 105906517A
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decanedioic acid
diethylaminoethanol
double
plant growth
preparation
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CN105906517B (en
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王彦林
王浩
王洋
陆硕文
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Shaanxi Gengyuan Ecological Agriculture Co ltd
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Suzhou University of Science and Technology
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02Compounds 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
    • C07C219/04Compounds 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
    • C07C219/06Compounds 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 the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41Preparation of salts of carboxylic acids
    • C07C51/412Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235Saturated compounds containing more than one carboxyl group
    • C07C59/245Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/265Citric acid

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Abstract

The invention relates to a plant growth regulator decanedioic acid double diethylamine alcohol ester citrate compound and a preparation method thereof. The structure of the compound is as shown in a formula stated in the specification. The preparation method comprises the following steps: in a reactor containing a water konckout vessel and a reflux device, carrying out reflux water reaction on decanedioic acid and N,N-diethylaminoethanol in an organic solvent in the presence of a catalyst at 110-150 DEG C to obtain decanedioic acid double diethylamine alcohol ester; and heating and melting decanedioic acid double diethylamine alcohol ester and 2fold mole of citric acid, and cooling and crystallizing under the stirring condition to obtain a white powdery solid product decanedioic acid double diethylamine alcohol ester citrate. The compound has an obvious promotion effect on rooting and sprouting of seeds; the stress resistance of the seeds can be improved; the plant growth regulator is high in activity, has anti-mold and bactericidal effects, is nontoxic and friendly to the environment; the production technology is simple; the cost is low; and industrial production is easy to implement.

Description

Double Diethylaminoethanol ester citrate compound of plant growth regulator decanedioic acid and preparation method thereof
Technical field
The present invention relates to double Diethylaminoethanol ester citrate compound of a plant growth regulators decanedioic acid and preparation method thereof.This compound has promotion seed germination, promotes plant growth, strengthens photosynthesis, improves crop yield, improve fruit quality and strengthen the purposes such as stress resistance of plant.
Background technology
Plant growth regulator has that consumption is little, it is big, effective to act on, can stratification, control to bloom, delaying senility course, raising yield, improve crop quality, increase resistance etc..Thus plant growth regulator has been the important component part of modern, and it is widely used.
Up to the present the commercialization plant growth regulator of most of China is still based on imitated kind, such as gibberellin, ethephon (CEPHA),2-(chloroethyl) phosphonic acid, NAA, IAA, 6-benzyl aminopurine (6-BA) and DA-6 etc., it is not ideal mostly to there is using effect in above-mentioned these, broad spectrum activity is the widest, safety in utilization difference or relatively costly etc. the shortcoming used, do not catch up with the paces that China's agriculture and forestry are fast-developing, and China has the of less types of independent intellectual property right, the level of China to be improved pesticide industry, urgently develop some low costs, effective, broad spectrum activity width, the new plant growth regulator that toxicity is little.On the other hand, along with on the earth, arable area reduces increasingly, population is growing, taking place frequently plus natural calamity, the yield per unit area how improving limited arable land is the key point solving mankind's food supply problem, and plant growth regulator increasingly receives publicity in terms of Ensuring Food Safety and raising yield.
Inventor is according to N, N-diethyl-2-(3,4-dichlorophenoxy) ethamine (DCPTA) and the structure of caproic acid Diethylaminoethanol ester (DA-6), diethylamino ethoxy group and decanedioic acid are carried out split, i.e. obtains, containing double diethylamino ethoxy structures, there is bioactive compound decanedioic acid pair Diethylaminoethanol ester.It is polyfunctional group synergistic structure, can produce cooperative effect with the physiologically active of diethylamino ethoxy so that it is have more excellent plant growth regulation.
Summary of the invention
An object of the present invention is that proposing one has the double Diethylaminoethanol ester citrate of bioactive compound decanedioic acid.This compound has simple in construction, soluble in water, is easily entered in cell body by cell membrane.Having amount of application compared with existing plant growth regulator few, effect is notable, low toxicity, and environmentally safe can overcome deficiency of the prior art.
For achieving the above object, present invention employs following technical scheme:
The double Diethylaminoethanol ester citrate compound of a kind of decanedioic acid, it is characterised in that the structure of this compound is shown below:
It is another object of the present invention to propose the preparation method of the double Diethylaminoethanol ester citrate of a kind of decanedioic acid.Its technique is simple, it is easy to large-scale production, and cheaper starting materials is easy to get, and equipment investment is few, with low cost, and atom utilization is high, and environmental pollution is little, and the method is:
A certain amount of organic solvent is added in the reactor equipped with water knockout drum and reflux, proper catalyst, add decanedioic acid and the N of certain mol proportion, N-diethylaminoethanol, the lower heating of stirring, reflux water-dividing reaction at a temperature of 110 DEG C~150 DEG C, reaction 5~9h, until the water separated reaches theoretical amount, Filtration of catalyst (reclaims and uses), filtrate decompression distills out organic solvent (reclaim and use), the diethylaminoethanol (reclaim and use) of excess and low boilers, bottoms adds the double Diethylaminoethanol ester Theoretical Mass 5%-10% activated decoloration of decanedioic acid, stir 30 minutes, filter to obtain the double Diethylaminoethanol ester of pale yellowish oil liquid decanedioic acid.Again the citric acid of double for decanedioic acid Diethylaminoethanol esters with twice mole is put in reactor, be heated with stirring to 100 DEG C, after citric acid melts, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powder solid product decanedioic acid.
A certain amount of organic solvent described above is dimethylbenzene or toluene, and its consumption volume milliliter number is 1-8 times of decanedioic acid quality grams.
Decanedioic acid and N, the N-diethylaminoethanol of certain mol proportion as above are decanedioic acid: the mol ratio of N, N-diethylaminoethanol is 1:2-1:3.
Proper catalyst as above is titanyl sulfate, titanium dioxide or silica gel, and its consumption is the 2%-10% of decanedioic acid quality grams.
The double Diethylaminoethanol ester of decanedioic acid of the present invention is pale yellowish oil liquid, water insoluble, index of refraction: nD 25=1.6629, density (20 DEG C): 0.8255g/cm3;Productivity is 83.6%~92.6%;The double Diethylaminoethanol ester citrate compound of decanedioic acid is white powdery solids, and fusing point is 98 DEG C, soluble in water.
The preparation principle of the double Diethylaminoethanol ester citrate compound of decanedioic acid is shown below:
Compared with prior art, the invention have benefit that:
(1) containing Liang Ge diethylaminoethanol ester functional group in one molecule of present configuration, with recessive decanedioic acid active body structure carrier each other, atom utilization is high, and active function groups superposition produces cooperative effect, it can play excellent plant growth regulation so that it is active effect significantly improves.
(2) the compounds of this invention has promotion seed germination, promotes plant growth, strengthens photosynthesis, improves crop yield, improve fruit quality and strengthen the effect such as stress resistance of plant, and it is of many uses, for broad spectrum type active regulator.
(3) to have consumption few for the compounds of this invention, the advantages such as toxicity is little, free from environmental pollution.
(4) Diethylaminoethanol of the compounds of this invention preparation technology used catalyst and solvent and excess is all directly to reclaim use, does not produce pollution, does not cause waste, belongs to green preparation process.
(5) when catalyst made by the compounds of this invention preparation technology silica gel, self there is decolorization, the decolorization to product can be saved.
(6) the compounds of this invention preparation method is simple, and cheaper starting materials is easy to get, low cost, and equipment investment is few, it is easy to large-scale production, has good application and development prospect.
Accompanying drawing explanation
Structure and performance spy in order to further illustrate product provide drawings described below.
Fig. 1 is the infrared spectrogram of the double Diethylaminoethanol ester of decanedioic acid;Fig. 1 shows, at 1750cm-1Near occur in that strong absworption peak, correspond to the stretching vibration of ester carbonyl group;Additionally, 2900cm-1Near CH occurs2The stretching vibration of middle c h bond;At 1350cm-1Near the stretching vibration of C-N-C key occurs.
Fig. 2 is the nuclear magnetic spectrum figure of the double Diethylaminoethanol ester of decanedioic acid;Fig. 2 shows, deuterochloroform is solvent, and δ 0.98 ~ 1.06 is N-(CH2CH3)2In methyl hydrogen peak;δ 1.25 ~ 1.35 is methylene peak;δ 1.50 ~ 1.65 is methylene peak;δ 2.25 ~ 2.36 is methylene peak;δ 2.50 ~ 2.65 is N-(CH2CH3)2The methylene hydrogen peak being connected with nitrogen;δ 2.67 ~ 2.72 is-OCH2CH2Methylene hydrogen peak that-N is connected with nitrogen and O=CCH2CH2CH2CH2CH2CH2CH2CH2The methylene hydrogen peak that C=O is connected with carbonyl;δ 4.12 ~ 4.19 is-OCH2CH2The methylene hydrogen peak that N is connected with oxygen.
Detailed description of the invention
Below in conjunction with specific embodiment, technical scheme is described further.
Embodiment 1 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 20ml dimethylbenzene, it is heated with stirring to 150 DEG C of back flow reaction 5h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g atlapulgite to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 37.04g of pale yellowish oil liquid decanedioic acid, productivity 92.6%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 2 is addition 20.2g (0.1mol) decanedioic acid in the 250ml four-hole boiling flask equipped with agitator and water knockout drum and reflux, and 23.4 G (0.2mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 40ml dimethylbenzene, it is heated with stirring to 140 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, after decompression distilling off solvent (reclaim and use) and low boilers, add 3.0g atlapulgite and stir 30 minutes, be cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 33.72g of pale yellowish oil liquid decanedioic acid, productivity 84.3%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 3 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.8g titanium dioxide, 20ml dimethylbenzene, it is heated with stirring to 150 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g atlapulgite to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 35.52g of pale yellow oily liquid body decanedioic acid, productivity 88.8%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 4 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 0.6g titanyl sulfate, 40ml dimethylbenzene, it is heated with stirring to 140 DEG C of back flow reaction 7h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g atlapulgite to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 34.32g of pale yellowish oil liquid decanedioic acid, productivity 85.8%.The citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 5 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 1.0g silica gel, 40ml dimethylbenzene, it is heated with stirring to 140 DEG C of back flow reaction 6h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, obtain the double Diethylaminoethanol ester 34.20g of pale yellowish oil liquid decanedioic acid, productivity 85.5%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 6 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.7g titanyl sulfate, 30ml toluene, it is heated with stirring to 120 DEG C of back flow reaction 6h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g atlapulgite to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 34.52g of pale yellowish oil liquid decanedioic acid, productivity 86.3%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 7 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 35.1g (0.3mol) N, N-diethylaminoethanol, 0.8g titanium dioxide, 30ml toluene, it is heated with stirring to 120 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g atlapulgite to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 34.6g of pale yellowish oil liquid decanedioic acid, productivity 86.5%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 8 is addition 20.2g (0.1mol) decanedioic acid in the 250ml four-hole boiling flask equipped with agitator and water knockout drum and reflux, and 23.4 G (0.2mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 40ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 10h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, after decompression distilling off solvent (reclaim and use) and low boilers, add 3.0g atlapulgite and stir 30 minutes, be cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 33.44g of pale yellowish oil liquid decanedioic acid, productivity 83.6%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain white powdery solids product.Its fusing point: 98 DEG C.
Embodiment 9 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 0.8g titanyl sulfate, 40ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 7h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, add 3.0g atlapulgite to stir 30 minutes, it is cooled to less than 80 DEG C, filter to obtain the double Diethylaminoethanol ester 33.64g of pale yellowish oil liquid decanedioic acid, productivity 84.1%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Embodiment 10 is adding 20.2g (0.1mol) decanedioic acid equipped with agitator in the 250ml four-hole boiling flask of water knockout drum and reflux, 29.3g (0.25mol) N, N-diethylaminoethanol, 1.0g silica gel, 40ml toluene, it is heated with stirring to 110 DEG C of back flow reaction 8h, until separating 3.6g (0.2mol) water, Filtration of catalyst (direct reuse), filtrate proceeds in the there-necked flask of another 250ml, decompression distilling off solvent (reclaims and uses), after the diethylaminoethanol (reclaim and use) of excess and low boilers, obtain the double Diethylaminoethanol ester 34.12g of pale yellowish oil liquid decanedioic acid, productivity 85.3%.Again the citric acid mix and blend of double for decanedioic acid Diethylaminoethanol esters with twice mole is heated to 100 DEG C, after making citric acid melt, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white powdery solids product decanedioic acid.Its fusing point: 98 DEG C.
Table 1 decanedioic acid is that main technologic parameters prepared by raw material
Double for the decanedioic acid of preparation Diethylaminoethanol ester citric acid hydrochlorates are also used for green vegetables, soya bean, wheat, rape, rice paddy seed with reference to " international seed inspection procedure " (1985), " crop seeds inspection procedure " (1995) as evaluating the standard (to grow 1cm for germinateing) whether seed germinates by inventor, having made biological activity test, method of testing is as follows:
Use plate culture, double for decanedioic acid Diethylaminoethanol ester citrates are configured to respectively the solution of 100mg/L, 70mg/L, 40mg/L and 10mg/L variable concentrations, study it to green vegetables, soya bean, wheat, rape, the growth regulating effect of rice seedling root system.Blank test is made with distilled water, the DA-6 solution of same concentrations makees standard control group, green vegetables, soya bean, wheat, rape, rice paddy seed 6h 8h is soaked respectively with the solution of respective concentration, then be respectively placed in temperature be 23 DEG C, 25 DEG C, 20 DEG C, 23 DEG C, 28 DEG C of incubated rooms measure the length of its root system and stem after cultivating 4d 6d, and add up germination number, calculate germination percentage and regulation percent activity by below equation.
Germination percentage=germinative number/seed sum
A=(N-N0)/N0×100%
A is sample regulation activity;
N cultivates the overall average length of the root recorded and bud in compound solution;
N0 cultivates the overall average length of the root recorded and bud in distilled water;
The double Diethylaminoethanol ester citrate of decanedioic acid prepared by the present invention is shown in Table 2 respectively to the data of plant growth regulating activity and germination percentage, shown in table 3, table 4, table 5 and table 6.
The double Diethylaminoethanol ester citrate of table 2 decanedioic acid is for green vegetables seed (50) Seed germination data
The double Diethylaminoethanol ester citrate of table 3 decanedioic acid is for soya bean seed (10) Seed germination data
The double Diethylaminoethanol ester citrate of table 4 decanedioic acid is for wheat seed (30) Seed germination data
The double Diethylaminoethanol ester citrate of table 5 decanedioic acid is for rape seed (50) Seed germination data
The double Diethylaminoethanol ester citrate of table 6 decanedioic acid is for rice paddy seed (30) Seed germination data

Claims (6)

1. the double Diethylaminoethanol ester citrate compound of a plant growth regulators decanedioic acid, it is characterised in that the structure of this compound is shown below:
2. the preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators decanedioic acid, it is characterised in that the method is:
A certain amount of organic solvent is added in the reactor equipped with water knockout drum and reflux, proper catalyst, control decanedioic acid and N, N-diethylaminoethanol mol ratio 1:2-1:3, the lower heating of stirring, reflux water-dividing reaction 5-10h at a temperature of 110-150 DEG C, until separating the water of theoretical amount, Filtration of catalyst, filtrate decompression distills out organic solvent, the diethylaminoethanol of excess and low boilers, bottoms adds the activated decoloration of the double Diethylaminoethanol ester Theoretical Mass 5%-10% of decanedioic acid, stir 30 minutes, filter to obtain the double Diethylaminoethanol ester of pale yellowish oil liquid decanedioic acid;Again the citric acid of double for decanedioic acid obtained above Diethylaminoethanol esters with twice mole is put in reactor, be heated with stirring to 100 DEG C, after citric acid melts, the lower crystallisation by cooling of stirring, i.e. obtain the double Diethylaminoethanol ester citrate of white solid product decanedioic acid.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators decanedioic acid the most according to claim 2, it is characterized in that: described organic solvent is dimethylbenzene or toluene, its consumption volume milliliter number is 1-8 times of decanedioic acid quality grams.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators decanedioic acid the most according to claim 2, it is characterized in that: the decanedioic acid of described certain mol proportion and N, N-diethylaminoethanol is decanedioic acid: the mol ratio of N, N-diethylaminoethanol is 1: 2-1: 3.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators decanedioic acid the most according to claim 2, it is characterized in that: described proper catalyst is titanyl sulfate, titanium dioxide or silica gel, its consumption is the 2%-10% of decanedioic acid quality.
The preparation method of the double Diethylaminoethanol ester citrate compound of a plant growth regulators decanedioic acid the most according to claim 2, it is characterized in that: described Filtration of catalyst, filtrate decompression distill out organic solvent, excess diethylaminoethanol be recovered to catalyst, organic solvent, diethylaminoethanol recycling.
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Publication number Priority date Publication date Assignee Title
CN108558683A (en) * 2018-05-09 2018-09-21 青岛科技大学 2- (2- diethylamino ethoxies) -5- nitrophenols and its preparation method and application

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