CN107488166A - It is a kind of to be used for bactericide of sulfate reducing bacteria and preparation method thereof in oilfield sewage - Google Patents
It is a kind of to be used for bactericide of sulfate reducing bacteria and preparation method thereof in oilfield sewage Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/10—Nature of the water, waste water, sewage or sludge to be treated from quarries or from mining activities
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/04—Disinfection
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- C—CHEMISTRY; METALLURGY
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/07—Optical isomers
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Abstract
The invention belongs to disposing polluted water in oil technical field, it is used for bactericide of sulfate reducing bacteria and preparation method thereof in oilfield sewage more particularly to a kind of, the bactericide is by 1 propyl alcohol and 2,2,6 trimethyls 41, the reactive ketone of 3 dioxocyclohex alkene 4 generates intermediate, is then split using chiral reagent, obtains final bactericide.1 described propyl alcohol and the mol ratio of the ketone of 2,2,6 trimethyl, 4 1,3 dioxocyclohex alkene 4 are 1:0.8~1.2, preferably 1:0.9.The needs that raw material sources are extensive, synthesis technique is simple, strong adaptability, oil field development can be met of the bactericide of the present invention；The bactericide of the present invention has the characteristics of low usage amount, Small side effects and non-environmental-pollution；The bactericide of the present invention has the characteristics of sterilizing rate is high simultaneously, reaches more than 98% to the sterilizing rate of sulfate reducing bacteria in oilfield sewage.Therefore, present invention is generally applicable in the sterilization processing technique of oilfield sewage.
Description
Technical field
The present invention relates to disposing polluted water in oil technical field, and in particular to one kind is used for sulfate reducing bacteria in oilfield sewage
Bactericide and preparation method thereof.
Background technology
Often contain substantial amounts of bacterium in oil field flood pattern, such as sulfate reducing bacteria (SRB), saprophytic bacteria (TGB), iron bacteria
(FB), sulfur bacteria, mould etc., wherein it is sulfate reducing bacteria, saprophytic bacteria and iron bacteria to endanger maximum bacterium to oil field.Bacterium
Harm of the activity to oil field be mainly shown as three aspects:(1) to the corrosion of equipment and pipeline；(2) deteriorate injection water quality,
Block flood pattern and stratum；(2) bacterium may degrade water treatment agent, chemicals treatment efficiency is reduced or even is failed.
Sulfate reducing bacteria is a kind of Anaerobic Bacteria, in the aerobic flood pattern of open type, although containing a certain amount of in water
Dissolved oxygen, but water is after water injecting pump pressurizes, into closed system.The dissolved oxygen in water can be gradually used up due to saprophytic bacteria, it is special
It is not to be covered with some sloughs and dirt below thing, local anaerobic area can be formed, provided for the growth of sulfate reducing bacteria
Anaerobic condition, sulfate reducing bacteria also can growth and breedings in aerobic flood pattern.Sulfate reducing bacteria is in growth and breeding process
In, sulfate radical in reductive water, acted on by producing cathodic depolarization, release hydrogen sulfide simultaneously produces concentration polarization, formed electrode so as to
Accelerate steel corrosion, flood pattern so-called " Heisui River " phenomenon is occurred, deteriorate water quality, make content of impurities increase in water.It is logical
Carry out sterilization processing frequently with effective bactericide and control bacterial growth, each specific injection wet concentration is selected high treating effect,
The bactericide of high financial profit is particularly important.
The method of oil field control sulfate reducing bacteria can be divided into physical method and the major class of chemical method two.Physical method has purple
The methods of outside line irradiation, plasma method, ultrasonic sterilization.Chemical method has change media environment, the methods of adding bactericide.Thing
Be present operating cost height in the sterilization of reason method, consume energy the shortcomings of big, the less use in actual job.Add the method tool of bactericide
Have it is economical, conveniently, it is quick the features such as, therefore in the operation of China's oil industry produce reality, always as main processing
Means.
Oil field, which is mainly taken, at present adds dodecyl benzyl dimethyl ammonium chloride " 1227 " preventing and treating sulfate reducing bacteria, by
In long-term use, make SRB to which creating a certain degree of resistance to the action of a drug.Battalion of gold in 2004 et al. have studied bi-quaternary ammonium salt chemical combination
Thing is as Germicide for Sulfate Reduction Bacteria, and the studies have shown that bactericide has the features such as bactericidal effect is good, and toxicity is low, but season
The bactericide of ammonium salt class also has deficiency, and containing many suspended particulates, the electronegative material of emulsified oil bead in such as water filling, they are all
It can be interacted with quaternary ammonium salt, it is lowered its bactericidal activity or even mistake from producing electrostatic attraction effect with cell membrane
Effect.
The content of the invention
The present invention provides for the deficiency of currently available technology a kind of to be used for sulfate reducing bacteria in oilfield sewage and kills
Microbial inoculum and preparation method thereof, the bactericide has the characteristics of preparation technology is simple, sterilization of high efficiency, low toxicity, stability are good, to sulphur
The sterilizing rate of hydrochlorate reducing bacteria reaches more than 98%.
It is an object of the invention to provide a kind of bactericide for being used for sulfate reducing bacteria in oilfield sewage, the bactericide is
By 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- reactive ketones generation intermediate, then entered using chiral reagent
Row is split, and obtains final bactericide, its molecular formula is as follows：
The mol ratio of described 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone is 1:0.8~1.2,
Yield is 90.0%~95.0%, preferably 1:0.9, yield 95.0%.
It is another object of the present invention to provide a kind of preparation for being used for Germicide for Sulfate Reduction Bacteria in oilfield sewage
Method, described preparation method specifically include following steps：
(1) the 1- propyl alcohol and 2 of aforementioned proportion is weighed, 2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone, is placed into four
In mouth flask, solvent xylene is added, is then to slowly warm up to 50~70 DEG C, stir speed (S.S.) is 200~350rpm, to be dissolved complete
Quan Hou, catalyst being added, then raises temperature to 140~145 DEG C, stir speed (S.S.) is constant, 5~10h of back flow reaction, is cooled to room temperature,
Beta-amino ethyl crotonate and 2- pyrrole aldehydes are added, is heated to 80~90 DEG C, stir speed (S.S.) is 300~350 DEG C, continues to react
6~8h, obtain yellow intermediate product solution；
(2) chiral reagent being added in above-mentioned intermediate product solution, is warming up to 60~80 DEG C, stir speed (S.S.) is 300~
450rpm, after chiral reagent is completely dissolved, 140~145 DEG C are warming up to again, stir speed (S.S.) is down to 250~350rpm, reaction
6~12h, room temperature is then cooled to, stands 1d, obtain the crude product in solution of the present invention；
(3) above-mentioned crude product in solution is filtered, filter cake is washed 2~3 times with absolute ethyl alcohol, and gained solid is added into quality
Concentration is in 10% sodium hydroxide solution, stirs 10~15min, liquid separation, and aqueous phase adds 6mol/L concentrated hydrochloric acid to make its pH=3, analyses
Go out yellow insoluble matter, suction filtration obtains yellow solid, is the bactericide of the present invention.
Wherein, described solvent xylene dosage is 5~10 times of 1- propyl alcohol quality；Described catalyst is dimethyl methyl
Acid amides, dosage are the 1~1.5% of 1- propyl alcohol quality；The dosage of described beta-amino ethyl crotonate for 1- propyl alcohol quality 3~
8 times；The dosage of described 2- pyrrole aldehydes is 3~8 times of 1- propyl alcohol quality；Described chiral reagent is quinindium or Xin Keni
Fourth, dosage are 10~15 times of 1- propyl alcohol quality；The dosage of described sodium hydroxide solution is 8~18 times of 1- propyl alcohol quality.
Described reaction equation is as follows：
The present invention is provided to the bactericide of sulfate reducing bacteria in oilfield sewage, the bactericide belongs to nonionic chemical combination
Thing, externally in electroneutral, it is not easy to negative ions and combines failure；The molecule contains secondary amine group, can be adsorbed on bacterial cell table
Face, so as to change the electrical conductance of cell membrane, surface tension, dissolubility etc., make protein denaturization, suppress or stimulate the activity of enzyme,
The plasmalemma of control infringement cell permeability, so as to kill sulfate reducing bacteria.There are double secondary amine groups and double on the molecule
Ester group, solves that conventional sterilants dosage is bigger than normal, the not high problem of sterilizing rate.
The present invention has the following advantages that compared with prior art and beneficial effect：
(1) raw material sources of bactericide of the invention are extensive, synthesis technique is simple, and yield is high, reaches more than 90%；
(2) bactericide of the invention has that usage amount is low, Small side effects, strong adaptability, the characteristics of non-environmental-pollution, can expire
The needs of sufficient oil field development；
(3) bactericide of the invention has the characteristics of sterilizing rate is high, to the sterilizing rate of sulfate reducing bacteria in oilfield sewage
Reach more than 98%.
Embodiment
The present invention is described in further detail with reference to specific embodiment, and with reference to data.It should be understood that these embodiments
It is of the invention solely for the purpose of illustration, rather than the scope limiting the invention in any way.
Embodiment 1：Degreaser M1And preparation method thereof
(1) bactericide M1Composition, component and molecular formula it is as follows：
Bactericide M1It is to generate intermediate by 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- reactive ketones,
Then split using chiral reagent, obtain final bactericide, its molecular formula is as follows：
The mol ratio of described 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone is 1:0.8.
(2) bactericide M1Preparation method it is as follows：
1. weighing 1mol 1- propyl alcohol and 0.8mol 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone, it is placed into
In four-hole boiling flask, 300.5g solvent xylenes are added, are then to slowly warm up to 50 DEG C, stir speed (S.S.) 200rpm is to be dissolved complete
Quan Hou, 0.601g dimethylformamides are added, then raise temperature to 140 DEG C, stir speed (S.S.) is constant, back flow reaction 5h, is cooled to room
Temperature, 180.3g beta-aminos ethyl crotonate and 180.3g 2- pyrrole aldehydes being added, be heated to 80 DEG C, stir speed (S.S.) is 300 DEG C,
Continue to react 7h, obtain yellow intermediate product solution；
2. 601g quinindiums are added in above-mentioned intermediate product solution, 60 DEG C are warming up to, stir speed (S.S.) 300rpm, is treated
After chiral reagent is completely dissolved, 140 DEG C are warming up to again, stir speed (S.S.) is down to 250rpm, reacts 6h, is then cooled to room temperature,
1d is stood, obtains the crude product in solution of the present invention；
3. above-mentioned crude product in solution is filtered, filter cake is washed 2 times with absolute ethyl alcohol, and gained solid is added into 480.8g matter
It is in 10% sodium hydroxide solution to measure concentration, stirs 10min, liquid separation, and aqueous phase adds 6mol/L concentrated hydrochloric acid to make its pH=3, separates out
Yellow insoluble matter, suction filtration obtain yellow solid, are the bactericide M of the present invention1, M1Yield be 92.4%.
Generate bactericide M1Reaction equation it is as follows：
Embodiment 2：Degreaser M2And preparation method thereof
(1) bactericide M2Composition, component and molecular formula it is as follows：
Bactericide M2It is to generate intermediate by 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- reactive ketones,
Then split using chiral reagent, obtain final bactericide, its molecular formula is as follows：
The mol ratio of described 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone is 1:0.9.
(2) bactericide M2Preparation method it is as follows：
1. weighing 1mol 1- propyl alcohol and 0.9mol 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone, it is placed into
In four-hole boiling flask, 480.8g solvent xylenes are added, are then to slowly warm up to 60 DEG C, stir speed (S.S.) 350rpm is to be dissolved complete
Quan Hou, 0.721g dimethylformamides are added, then raise temperature to 143 DEG C, stir speed (S.S.) is constant, back flow reaction 8h, is cooled to room
Temperature, 480.8g beta-aminos ethyl crotonate and 360.6g 2- pyrrole aldehydes being added, be heated to 85 DEG C, stir speed (S.S.) is 320 DEG C,
Continue to react 6h, obtain yellow intermediate product solution；
2. 800g cinchonidines are added in above-mentioned intermediate product solution, 80 DEG C, stir speed (S.S.) 380rpm are warming up to,
After chiral reagent is completely dissolved, 142 DEG C are warming up to again, and stir speed (S.S.) is down to 350rpm, reacts 10h, is then cooled to room
Temperature, 1d is stood, obtain the crude product in solution of the present invention；
3. above-mentioned crude product in solution is filtered, filter cake is washed 3 times with absolute ethyl alcohol, and gained solid is added into 750.5g matter
It is in 10% sodium hydroxide solution to measure concentration, stirs 12min, liquid separation, and aqueous phase adds 6mol/L concentrated hydrochloric acid to make its pH=3, separates out
Yellow insoluble matter, suction filtration obtain yellow solid, are the bactericide M of the present invention2, M2Yield be 95.0%.
Generate bactericide M2Reaction equation as shown in Example 1.
Embodiment 3：Degreaser M3And preparation method thereof
(1) bactericide M3Composition, component and molecular formula it is as follows：
Bactericide M3It is to generate intermediate by 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- reactive ketones,
Then split using chiral reagent, obtain final bactericide, its molecular formula is as follows：
The mol ratio of described 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone is 1:1.2.
(2) bactericide M3Preparation method it is as follows：
1. weighing 1mol 1- propyl alcohol and 1.2mol 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone, it is placed into
In four-hole boiling flask, add 601g solvent xylenes, be then to slowly warm up to 70 DEG C, stir speed (S.S.) 300rpm, it is to be dissolved completely
Afterwards, 0.901g dimethylformamides are added, then raise temperature to 145 DEG C, stir speed (S.S.) is constant, back flow reaction 10h, is cooled to room
Temperature, 300.5g beta-aminos ethyl crotonate and 480.8g2- pyrrole aldehydes being added, be heated to 90 DEG C, stir speed (S.S.) is 350 DEG C, after
Continuous reaction 8h, obtains yellow intermediate product solution；
2. 901.5g quinindiums are added in above-mentioned intermediate product solution, 72 DEG C, stir speed (S.S.) 450rpm are warming up to,
After chiral reagent is completely dissolved, 145 DEG C are warming up to again, and stir speed (S.S.) is down to 300rpm, reacts 12h, is then cooled to room
Temperature, 1d is stood, obtain the crude product in solution of the present invention；
3. above-mentioned crude product in solution is filtered, filter cake is washed 2 times with absolute ethyl alcohol, and gained solid is added into 1081.8g
Mass concentration is in 10% sodium hydroxide solution, stirs 15min, liquid separation, and aqueous phase adds 6mol/L concentrated hydrochloric acid to make its pH=3, analyses
Go out yellow insoluble matter, suction filtration obtains yellow solid, is the bactericide M of the present invention3, M3Yield be 90.0%.
Generate bactericide M3Reaction equation as shown in Example 1.
The Lab-evaluation of embodiment 4 is tested
Shengli Oil Field multi-purpose station K12The sewage of processing is sewage after water drive Produced Liquid water-oil separating, SRB (sulfuric acid in sewage
Salt reducing bacteria) 10000/mL of content, the concentration for adding bactericide in the sewage after bactericide is 50mg/L, according to standard Q/
The oil field produced water process bactericide general technical specifications of SH1020 0688-2013 has carried out sterilization to the bactericide of the present invention
Effect assessment, it the results are shown in Table 1.
As it can be seen from table 1 bactericide M1、M2And M3Handle Shengli Oil Field multi-purpose station K12The sterilizing rate of sewage is respectively
99.0%th, 99.5% and 98.5%, sterilizing rate is all higher than 98.0%, and bactericidal effect is good.
The bactericide M of table 11、M2And M3Handle the sterilizing rate of sewage
| Sequence number | Bactericide | After processing, individual/ml | Sterilizing rate, % |
| 1 | M1 | 100 | 99.0 |
| 2 | M2 | 50 | 99.5 |
| 3 | M3 | 150 | 98.5 |
The bactericide M of embodiment 51Field application
Shengli Oil Field multi-purpose station B1The sewage of processing is sewage after water drive Produced Liquid water-oil separating, and day output is
1200m3/ d, SRB (sulfate reducing bacteria) 10000/mL of content in sewage, adds bactericide M1Bactericide in sewage afterwards
Concentration is 30mg/L, day dosage be 36kg, SRB (sulfate reducing bacteria) content is 150/mL after processing, and sterilizing rate is
98.5%, bactericide M1Field test bactericidal effect it is good.
The bactericide M of embodiment 62Field application
Shengli Oil Field multi-purpose station B7The sewage of processing is sewage after water drive Produced Liquid water-oil separating, and day output is
1000m3/ d, SRB (sulfate reducing bacteria) 25000/mL of content in sewage, add the dense of bactericide in the sewage after bactericide
Spend for 50mg/L, day dosage be 50kg, SRB (sulfate reducing bacteria) content is 50/mL after processing, and sterilizing rate is
99.8%, bactericide M2Field test bactericidal effect it is good.
The bactericide M of embodiment 73Field application
Shengli Oil Field multi-purpose station B10The sewage of processing is sewage after water drive Produced Liquid water-oil separating, and day output is
800m3/ d, SRB (sulfate reducing bacteria) 20000/mL of content in sewage, add the dense of bactericide in the sewage after bactericide
Spend for 40mg/L, day dosage be 32kg, SRB (sulfate reducing bacteria) content is 100/mL after processing, and sterilizing rate is
99.5%, bactericide M3Field test bactericidal effect it is good.
Claims (9)
1. a kind of bactericide for being used for sulfate reducing bacteria in oilfield sewage, it is characterised in that described bactericide is by 1- third
Alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- reactive ketones generation intermediate, is then split using chiral reagent
Obtain, its molecular formula is as follows：
2. the bactericide according to claim 1 for being used for sulfate reducing bacteria in oilfield sewage, it is characterised in that described
The mol ratio of 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone is 1:0.8~1.2.
3. the bactericide according to claim 2 for being used for sulfate reducing bacteria in oilfield sewage, it is characterised in that described
The mol ratio of 1- propyl alcohol and 2,2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone is 1:0.9.
A kind of 4. preparation method for being used for the bactericide of sulfate reducing bacteria in oilfield sewage, it is characterised in that described preparation
Method specifically includes following steps：
(1) the 1- propyl alcohol and 2 of aforementioned proportion is weighed, 2,6- trimethyl -4-1,3- dioxocyclohex alkene -4- ketone, is placed into four mouthfuls of burnings
In bottle, solvent xylene is added, is then to slowly warm up to 50~70 DEG C, stir speed (S.S.) is 200~350rpm, to be dissolved complete
Afterwards, catalyst is added, then raises temperature to 140~145 DEG C, stir speed (S.S.) is constant, 5~10h of back flow reaction, is cooled to room temperature, adds
Enter beta-amino ethyl crotonate and 2- pyrrole aldehydes, be heated to 80~90 DEG C, stir speed (S.S.) is 300~350 DEG C, continues reaction 6
~8h, obtain yellow intermediate product solution；
(2) chiral reagent being added in above-mentioned intermediate product solution, is warming up to 60~80 DEG C, stir speed (S.S.) is 300~
450rpm, after chiral reagent is completely dissolved, 140~145 DEG C are warming up to again, stir speed (S.S.) is down to 250~350rpm, reaction
6~12h, room temperature is then cooled to, stands 1d, obtain the crude product in solution of the present invention；
(3) above-mentioned crude product in solution is filtered, filter cake is washed 2~3 times with absolute ethyl alcohol, and gained solid is added into mass concentration
In 10% sodium hydroxide solution, to stir 10~15min, liquid separation, aqueous phase adds 6mol/L concentrated hydrochloric acid to make its pH=3, separates out yellow
Color insoluble matter, suction filtration obtain yellow solid, are the bactericide of the present invention.
5. the preparation method according to claim 4 for being used for the bactericide of sulfate reducing bacteria in oilfield sewage, its feature
It is, described solvent xylene dosage is 5~10 times of 1- propyl alcohol quality.
6. the preparation method for being used for the bactericide of sulfate reducing bacteria in oilfield sewage according to claim 4 or 5, it is special
Sign is that described catalyst is dimethylformamide, and dosage is the 1~1.5% of 1- propyl alcohol quality.
7. the preparation method for being used for the bactericide of sulfate reducing bacteria in oilfield sewage according to claim 4 or 5, it is special
Sign is that the dosage of described beta-amino ethyl crotonate is 3~8 times of 1- propyl alcohol quality, and the dosage of 2- pyrrole aldehydes is 1-
3~8 times of propyl alcohol quality.
8. the preparation method for being used for the bactericide of sulfate reducing bacteria in oilfield sewage according to claim 4 or 5, it is special
Sign is that described chiral reagent is quinindium or cinchonidine, and dosage is 10~15 times of 1- propyl alcohol quality.
9. the preparation method for being used for the bactericide of sulfate reducing bacteria in oilfield sewage according to claim 4 or 5, it is special
Sign is that the dosage of described sodium hydroxide solution is 8~18 times of 1- propyl alcohol quality.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110845170A (en) * | 2019-11-15 | 2020-02-28 | 石家庄铁道大学 | Composite bactericide for concrete in sewage environment and screening method thereof |
| CN111296447A (en) * | 2020-03-24 | 2020-06-19 | 东营施普瑞石油工程技术有限公司 | Efficient bactericide for oil field and preparation method thereof |
| CN114736142A (en) * | 2022-06-09 | 2022-07-12 | 山东科兴化工有限责任公司 | Oil field sewage sterilization and degreasing agent, and synthetic method and application thereof |
-
2017
- 2017-08-25 CN CN201710740203.8A patent/CN107488166A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845170A (en) * | 2019-11-15 | 2020-02-28 | 石家庄铁道大学 | Composite bactericide for concrete in sewage environment and screening method thereof |
| CN111296447A (en) * | 2020-03-24 | 2020-06-19 | 东营施普瑞石油工程技术有限公司 | Efficient bactericide for oil field and preparation method thereof |
| CN114736142A (en) * | 2022-06-09 | 2022-07-12 | 山东科兴化工有限责任公司 | Oil field sewage sterilization and degreasing agent, and synthetic method and application thereof |
| CN114736142B (en) * | 2022-06-09 | 2022-09-02 | 山东科兴化工有限责任公司 | Oil field sewage sterilization and degreasing agent, and synthetic method and application thereof |
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