CN110498747A - A kind of tetramine baseline small molecule compound and its preparation method and application - Google Patents
A kind of tetramine baseline small molecule compound and its preparation method and application Download PDFInfo
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- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/13—Amines containing three or more amino groups bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
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- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/12—Swell inhibition, i.e. using additives to drilling or well treatment fluids for inhibiting clay or shale swelling or disintegrating
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Abstract
The present invention provides a kind of tetramine baseline small molecule compound and its preparation method and application.The chemical formula of the small molecule compound is C4H16N4, structural formula are as follows:Preparation method is by antierythrite initial oxidation into 2,3- dioxo butanedial, and then 2,3- dioxo butanedial and ammonium formate generation reduction amination obtain.The present invention also provides above-mentioned tetramine baseline small molecule compounds to inhibit the application in clay mineral aquation.Tetramine baseline small molecule intercalation inhibitor prepared by the present invention has the characteristics that molecular dimension and structure controllable precise, end group is primary amine group and groups density is big, there is stronger inhibition to the aquation pulping effect of bentonite and mud shale, hydration swelling can be effectively suppressed under lower dosage, and there is stronger heat-resisting property, temperature resistance is up to 220 DEG C.
Description
Technical field
The present invention relates to a kind of technologies of preparing of compound, and in particular to a kind of tetramine baseline small molecule compound and its
Preparation method and application.
Background technique
With the increasing to deep formation Oil And Gas Exploration And Development dynamics, drilling depth persistently increases, and it is de- containing covering to bore chance
The probability that stone and Iraq/Mongolia mix the hydration swellings type clay mineral stratum such as layer rises with it, and deep-well, ultradeep well lower part well section temperature
Higher, big well depth causes the circulation of drilling fluid time long again, is acted on by long term high temperature, and the inhibitor in drilling fluid system is difficult to stablize
Inhibit the hydration swelling and pulping of clay mineral, the unfavorable hole condition such as Yi Yinfa bit balling and creep reducing diameter seriously hinders drilling well
The progress of operation.
For inhibition clay mineral aquation, the amido intercalation inhibitor of low molecular weight need to be added into system, after its aquation,
Montmorillonite mineral interlamination region can be spread and be embedded under difference in chemical potential effect, amine groups (primary amine, secondary amine in inhibitor molecules
Deng) form hydrogen bond with the hydroxyl on montmorillonite crystal layer end face and connect, so that inhibitor molecules is adsorbed on crystal layer surface, squeezes out interlayer suction
Attached water tenses adjacent crystal layer simultaneously, realizes the inhibiting effect to the aquation pulping of clay mineral.Currently used amido intercalation suppression
Preparation is mostly double primary amine groups small molecules, such as ethylenediamine, butanediamine, hexamethylene diamine, or is polyethylene polyamine micromolecular, such as diethyl
Alkene triamine, triethylene tetramine, tetraethylenepentamine etc..When double primary amine groups small molecules enter mineral interlamination region, due to there was only molecule
The primary amine group at both ends has characterization of adsorption, therefore its limited sorption capacity, retardance hydrone is invasive can be limited, and hydrocarbon segment
Longer, hydrophobicity is stronger, is more likely formed bilayer or multi-molecular absorption pattern, can strut interlamellar spacing instead, leads to its suppression
Efficiency processed is limited, though and polyethylene polyamine can be located at the secondary amine group in hydrocarbon segment by it, realization occupied space volume is more
Small horizontal mono layer adsorption, but its expensive price limit application of this micromolecular in drilling fluid.
Therefore, contain amidine functional group in molecular chain-end and segment as polyethylene polyamine as can developing, together
Shi Chengben more cheap novel linear small molecule amido intercalation inhibitor, can not only be applied to more friendly to environment
High performance water-based drilling fluid system, while can also be used as underground Water-based working liquid for electrical that other need to inhibit clay mineral aquation (such as
Cementing fluid, well killing fluid, workover fluid, perforating fluid, packing fluid, acid solution, fracturing fluid and displacing fluid etc.) key assistant.
Summary of the invention
In view of the problems of the existing technology, the present invention provides a kind of tetramine baseline small molecule compound and its preparation side
Method and application.The technical solution of the present invention is as follows:
First aspect, the present invention provide a kind of tetramine baseline small molecule compound, chemical formula C4H16N4, structure
Formula are as follows:
The second aspect, the present invention provide the preparation method of above-mentioned tetramine baseline small molecule compound, are by erythrose
Alcohol initial oxidation is at 2,3- dioxo butanedial, and then 2,3- dioxo butanedial and ammonium formate generation reduction amination obtain.
Further, the preparation method comprises the following steps:
(1) PCC reagent is prepared；
(2) in organic solvent by antierythrite and the dissolution of PCC reagent, oxidation reaction, reaction knot are carried out under room temperature
It is purified after beam, obtains 2,3- dioxo butanedial；
(3) ammonium formate, formic acid and 2,3- dioxo butanedial are restored in organic solvent two in 140~160 DEG C
Aminating reaction purifies both obtained after reaction.
Further, the detailed process of PCC reagent prepare in the step (1) are as follows: by chromium trioxide be dissolved in concentration for 5~
In the hydrochloric acid solution of 8mol/L, mixed solution is then cooled to -2~0 DEG C, in pyridine is added in 10min, is protected in adition process
Holding system temperature is -2~0 DEG C, then 2~4h of insulation reaction, wherein in hydrochloric acid solution HCl, chromium trioxide and pyridine mole
Than for (0.5~1): 1:1 end of reaction is dried to obtain.
Further, in the step (2) organic solvent one be water removal after methylene chloride, chloroform or tetrahydro furan
It mutters.
Further, the molar ratio of step (2) mesoerythrit and PCC reagent is 1:(0.325~0.375).
Further, organic solvent two is toluene, tetrahydrofuran or n,N-Dimethylformamide in the step (3).
Further, ammonium formate, formic acid and 2 in the step (3), the molar ratio of 3- dioxo butanedial be 1:(2~
3): (1~2).
In terms of third, the present invention provides above-mentioned tetramine baseline small molecule compound or contains the small molecule compound
Intercalation inhibitor inhibit clay mineral aquation in application.
The beneficial effects of the present invention are:
(1) it is anti-successively to carry out oxidation reaction, amination using antierythrite as raw material to antierythrite in the solution by the present invention
It answers, to obtain final product.Entire technical process is simple, and raw material sources are extensive, and low in cost, mild condition, safety is good, and
High income is suitable for industrial production.
(2) there is the tetramine baseline small molecule intercalation inhibitor prepared by the present invention molecular dimension and structure accurately may be used
Control, end group are primary amine group and the big feature of groups density, are had to the aquation pulping effect of bentonite and mud shale relatively strong
Inhibition, can be effectively suppressed hydration swelling under lower dosage, and there is stronger heat-resisting property, temperature resistance is up to 220
℃。
Detailed description of the invention
Fig. 1 is the infrared spectrum spectrogram of 2 gained 2,3- dioxo butanedial of embodiment.
Fig. 2 is the infrared spectrum spectrogram of 3 gained 1,2,3,4- tetramino butane of embodiment.
Specific embodiment
In the description of the present invention, it should be noted that the person that is not specified actual conditions in embodiment, according to normal conditions or
The condition that manufacturer suggests carries out.Reagents or instruments used without specified manufacturer is that can be obtained by commercially available purchase
Conventional products.
The present invention is described in further details with specific embodiment with reference to the accompanying drawing, described is to solution of the invention
It releases rather than limits.
Embodiment 1
The present embodiment is the preparation embodiment of PCC reagent, it should be noted that in chemical field, PCC reagent i.e. three is aoxidized
The complexing salting liquid of chromium and pyridine in hydrochloric acid.
Preparation process is as follows: quickly into the hydrochloric acid (wherein containing the HCl of 1.1mol) that 184mL concentration is 6mol/L, side is stirred
100g chromium trioxide is added in side, and after 5min, homogeneous phase solution is cooled to 0 DEG C, obtains rufous liquid, and natural filtration removes insoluble
Object.Later, in 10min, 79.1g pyridine is added dropwise in the homogeneous phase solution, and control system temperature is at -2~0 DEG C, with
The addition of pyridine gradually has yellow solid precipitation, drips pyridine, is cooled to 0 DEG C again, obtains crocus solid, is leaked with sand core
Crocus solid product is collected by filtration in bucket.After product is placed in vacuum desiccator dry 1h, then it is placed on equipped with phosphorus pentoxide
Drier in air drying 48h, obtain the final products of 180g, i.e. PCC reagent, yield 84%.
Involved reaction equation is as follows:
Embodiment 2
The present embodiment is the preparation embodiment of 2,3- dioxo butanedial.
By methylene chloride (DCM) through anhydrous CaCl2Steamed again after drying, after PCC reagent is dissolved in the DCM after water is evaporated off again
And stir, in the three-necked flask for pouring into 500mL after PCC reagent is completely dissolved.Under the conditions of being stirred at room temperature into three-necked flask
The DCM solution of antierythrite is added dropwise, the molar ratio of the hydroxyl and PCC reagent that guarantee antierythrite is 1:1.5, is added dropwise subsequent
Stop reaction after continuous reaction 4h.Upper solution is poured out, lower layer's solid matter is washed 3 times with DCM, and upper solution and cleaning solution are closed
And solution successively uses saturation NaHCO after merging3Aqueous solution washing, uses anhydrous Na later2SO4It dries, filters after removing solvent, it is right
Residual solution is evaporated under reduced pressure, obtained white crystal i.e. 2,3- dioxo butanedial.
Involved reaction equation is as follows:
The DCM after water is evaporated off it should be noted that DCM employed in the present embodiment attaches most importance to.
Fig. 1 show the infrared spectrum spectrogram of 2,3- dioxo butanedial obtained by the present embodiment, to the characteristic absorption of map
Peak is analyzed as follows: 3423cm-1Place is the-stretching vibration absworption peak of OH in the enol form isomer of 2,3- dioxo butanedial；
287cm-1Place is the stretching vibration absworption peak of C=C in the enol form isomer of 2,3- dioxo butanedial；1714cm-1Place is aldehyde
The stretching vibration absworption peak of C=O in base；1413cm-1Place is that C-H stretches in the enol form isomer of 2,3- dioxo butanedial
Contracting vibration absorption peak；1264cm-1And 1065cm-1Place is respectively in enol form isomer-face of OH in and out-of-plane bending vibration
Peak.Due to target product 2, contains β-hydrogen in the molecular structure of 3- dioxo butanedial, therefore be also easy to produce aldehyde during the preparation process
The analysis result of enol form isomer, infrared spectrum spectrogram also demonstrates this point.By the INFRARED SPECTRUM of 2,3- dioxo butanedial
Thus figure infers, is consistent with target product structure it is found that with the molecular radical envisioned in its molecular structure.
Embodiment 3
The present embodiment is the preparation embodiment of 1,2,3,4- tetramino butane.
It is that 1:2 weighs ammonium formate and formic acid according to molar ratio, pours into excess toluene, be again stirring for uniformly after mixing evenly
It pours into the three-necked flask with condensing reflux pipe afterwards.After being warming up to 80 DEG C under the conditions of oil bath, 2 are added dropwise into three-necked flask,
The toluene solution of 3- dioxo butanedial, wherein the molar ratio of 2,3- dioxo butanedial and ammonium formate is 1.5:1.Wait drip
So that reaction solution system is to slowly warm up to 160 DEG C after finishing, stops reaction after the reaction was continued 6h, obtain black tars shape liquid, subtract
Pressure, which filters, removes black removal coke matter impurity, and obtained cleaner liquid is successively with saturation NaHCO3It is washed with saturation NaCl aqueous solution,
Liquid after layering carries out liquid separation with separatory funnel, and uses anhydrous Na2SO4Dry upper layer mother liquor, finally depressurizes residual solution
Distillation, obtained white needle-like crystals i.e. 1,2,3,4- tetramino butane (TABT).Using raw material antierythrite as evaluation criterion
Words, then 1,2,3,4- tetramino butane yields are up to 85.29%.
Reaction route is as follows:
Fig. 2 show the infrared spectrum spectrogram of 1,2,3,4- tetramino butane, is analyzed as follows to the characteristic absorption peak of map:
3392cm-1And 3182cm-1Place is the symmetrical stretching vibration absorption peak of the N-H in terminal primary amine group；2918cm-1And 2847cm-1
Place is-CH2Out-of-plane bending vibration absorption peak；1644cm-1Place is that the bending vibration of the N-H in terminal primary amine group absorbs
Peak；1418cm-1Place is the characteristic absorption peak of the C-N in tertiary amine group；1083cm-1Place is the flexible of C-N in terminal primary amine group
Vibration absorption peak；1727cm-1There is not the stretching vibration absworption peak of ester group in place, shows no longer to contain in the end-group structure of product
There is aldehyde radical.By the infrared spectrum of 1,2,3,4- tetramino butane it is found that with the molecular radical envisioned in its molecular structure, thus
Infer, is consistent with target product structure.
After successfully preparing 1,2,3,4- tetramino butane, according to its English name 1,2,3,4-
Tetraaminobutane can be referred to as TABT, hereafter refer to the product with TABT.
Embodiment 4
The present embodiment is influence embodiment of the TABT inhibitor prepared by embodiment 3 to bentonite pulping performance.
TABT is configured to the aqueous solution of various concentration, containing there are two the Putriscine (DAB) of primary amine groups, Yi Jihan
It is comparative sample there are two primary amine groups and both linear small molecules of the triethylene tetramine (TETA) of two tertiary amine groups.Concentration is identical
The aqueous solutions of three kinds of amido small molecules be respectively classified into four groups, will wherein one group be placed at room temperature, and according to Chinese people's republicanism
Centrifugal process in state oil and gas industry standard SY/T5971-1994 " water filling clay stabilizer method of evaluating performance ", is commented
TABT and DAB, TETA inhibit the ability of bentonite pulping before valence aging.By in other three groups of merging ageing cans, respectively 150
DEG C, taken out after heat rolling 16 hours under the conditions of 180 DEG C and 220 DEG C, be cooled to room temperature, also according to centrifugal process, after evaluating aging
TABT and DAB, TETA inhibit the ability of bentonite pulping.
Specific step is as follows:
1. weighing 0.50g In Xiazijie Region, xinjiang bentonite in powder, it is accurate to 0.01g, is fitted into 10mL centrifuge tube, is added 10mL's
Inhibitor solution sufficiently shakes up, and stores 2h at room temperature, is packed into centrifuge, is centrifugated in the case where revolving speed is 2000r/min
15min.Read it is bentonite inflated after volume V1；
2. repeating step 1., replace inhibitor solution, the swelling volume of measurement bentonite in water with 10mL deionized water
V2；
3. repeating step 1., replace inhibitor solution with 10mL kerosene, measures volume V of the bentonite in kerosene0。
Anti-dilative calculation formula is as follows:
Wherein: B- anti-dilative, unit: %；V1Swelling volume of the bentonite in inhibitor solution, unit: mL；V2It is swollen
The swelling volume of profit soil in deionized water, unit: mL；V0Swelling volume of the bentonite in kerosene, unit: mL.
Experimental result is shown in Table 1.It can be seen from the data in Table 1 that after before ageing, the intercalation inhibitor of three kinds of ultra-low moleculars
Bentonitic expansion rate can be greatly reduced, but under identical aging temperature and dosage, the inhibitory effect of TABT be better than DAB with
TETA, the TABT aqueous solution such as before aging 1.0% can control bentonitic anti-dilative 84% or more, even if old through 220 DEG C
After change, 1.5% TABT aqueous solution can also be controlled bentonitic anti-dilative 83% or more, show it in room temperature and high temperature ring
Bentonitic aquation pulping can be effectively suppressed in border.
Influence of the 1 inhibitor dosage of table to anti-dilative
Embodiment 5
The present embodiment is influence embodiment of the TABT inhibitor prepared by embodiment 3 to mud shale pulping performance.
TABT, DAB and TETA are configured to the aqueous solution of various concentration respectively, it is natural according to People's Republic of China's petroleum
TABT, DAB are evaluated in mud shale distributed test in gas professional standard SY/T5613-2000 " mud shale physicochemical property test method "
Inhibit the ability of drilling cuttings dispersion pulping with TETA.
Sichuan Longma small stream stratum mud shale drilling cuttings is taken to cross 6~10 meshes, drying to constant weight, weighs 50.0g, is added to
350mL in the ageing can of three kinds of different amido small molecule water solution of concentration, is divided into four groups, respectively in 105 DEG C, 150
DEG C, at 180 DEG C and 220 DEG C after aging 16h, take out ageing can, be cooled to room temperature, by tank liquid and mud shale pour into 40 mesh
Separating sieve in, clean 1min with tap water.Separating sieve and shale are put into togerther in drying box, dried at (105 ± 3) DEG C
4h takes out cooling, stands in air for 24 hours, weighs record data M, calculates rolling rate of recovery R.
Rolling rate of recovery calculation formula is as follows:
Wherein: R- cuttings recovery, unit: %；Drilling cuttings yield after the rolling of M- heat, unit: g.
Experimental result is shown in Table 2.It can be seen that under the conditions of identical aging temperature and dosage from the data in table 2, mud shale
Substantially it is higher than its rate of recovery in DAB and TETA aqueous solution in the rolling rate of recovery in TABT aqueous solution, works as aging temperature
When to be respectively 105 and 220 DEG C, rolling rate of recovery of the mud shale in the TABT aqueous solution that concentration is 1.5% is respectively
74.50% and 67.05%, the range of decrease is limited, shows that the water of mud shale still can be effectively suppressed in TABT in 220 DEG C of hot environment
Change dispersion, has excellent heat-resisting property.
Influence of the 2 inhibitor dosage of table to rolling rate of recovery
To sum up, there is the tetramine baseline small molecule intercalation inhibitor prepared by the present invention molecular dimension and structure accurately may be used
Control, end group are primary amine group and the big feature of groups density, are had to the aquation pulping effect of bentonite and mud shale relatively strong
Inhibition, can be effectively suppressed hydration swelling under lower dosage, and there is stronger heat-resisting property, temperature resistance is up to 220
℃。
Although the embodiments of the present invention has been shown and described above, it is to be understood that above-described embodiment is example
Property, it is not considered as limiting the invention, those skilled in the art within the scope of the invention can be to above-mentioned
Embodiment is changed, modifies, replacement and variant.
Claims (9)
1. a kind of tetramine baseline small molecule compound, which is characterized in that its chemical formula is C4H16N4, structural formula are as follows:
2. a kind of preparation method of tetramine baseline small molecule compound described in claim 1, which is characterized in that be by red moss
Sugar alcohol initial oxidation is at 2,3- dioxo butanedial, and then 2,3- dioxo butanedial and ammonium formate generation reduction amination obtain.
3. a kind of preparation method of tetramine baseline small molecule compound according to claim 2, which is characterized in that including
Following steps:
(1) PCC reagent is prepared；
(2) in organic solvent by antierythrite and the dissolution of PCC reagent, oxidation reaction is carried out under room temperature, after reaction
Purification, obtains 2,3- dioxo butanedial；
(3) by ammonium formate, formic acid and 2,3- dioxo butanedial in organic solvent two in 140~160 DEG C of progress reduction aminations
Reaction purifies both obtained after reaction.
4. a kind of preparation method of tetramine baseline small molecule compound according to claim 3, which is characterized in that described
The detailed process of PCC reagent is prepared in step (1) are as follows: chromium trioxide is dissolved in the hydrochloric acid solution that concentration is 5~8mol/L, so
Mixed solution is cooled to -2~0 DEG C afterwards, in pyridine is added in 10min, it is -2~0 DEG C that system temperature is kept in adition process,
Then 2~4h of insulation reaction, wherein the molar ratio of HCl, chromium trioxide and pyridine are (0.5~1) in hydrochloric acid solution: 1:1 reaction
It finishes and is dried to obtain.
5. a kind of preparation method of tetramine baseline small molecule compound according to claim 3, which is characterized in that described
Organic solvent one is methylene chloride, chloroform or the tetrahydrofuran after water removal in step (2).
6. a kind of preparation method of tetramine baseline small molecule compound according to claim 3, which is characterized in that described
The molar ratio of step (2) mesoerythrit and PCC reagent is 1:(0.325~0.375).
7. a kind of preparation method of tetramine baseline small molecule compound according to claim 3, which is characterized in that described
Organic solvent two is toluene, tetrahydrofuran or N,N-dimethylformamide in step (3).
8. a kind of preparation method of tetramine baseline small molecule compound according to claim 3, which is characterized in that described
The molar ratio of ammonium formate, formic acid and 2,3- dioxo butanedial is 1:(2~3 in step (3)): (1~2).
9. a kind of tetramine baseline small molecule compound described in claim 1 or the intercalation suppression containing the small molecule compound
Preparation is inhibiting the application in clay mineral aquation.
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| CN112341487B (en) * | 2020-10-12 | 2022-06-07 | 中国石油化工股份有限公司 | Hyperbranched polysiloxane blocking agent and preparation method thereof |
| CN113666837A (en) * | 2021-08-12 | 2021-11-19 | 怀化宝华生物科技有限公司 | Preparation method of 1, 4-dimethyl pentylamine hydrochloride |
| CN113666837B (en) * | 2021-08-12 | 2024-06-07 | 怀化宝华生物科技有限公司 | Preparation method of 1, 4-dimethyl pentylamine hydrochloride |
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