CN113651709A - Fatty amide propyl dimethyl tertiary amine and preparation method and application thereof - Google Patents
Fatty amide propyl dimethyl tertiary amine and preparation method and application thereof Download PDFInfo
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- -1 Fatty amide propyl dimethyl tertiary amine Chemical class 0.000 title claims abstract description 85
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 50
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 34
- 239000000194 fatty acid Substances 0.000 claims abstract description 34
- 229930195729 fatty acid Natural products 0.000 claims abstract description 34
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 238000007112 amidation reaction Methods 0.000 claims abstract description 22
- 238000004821 distillation Methods 0.000 claims abstract description 21
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004327 boric acid Substances 0.000 claims abstract description 12
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 106
- 239000002250 absorbent Substances 0.000 claims description 17
- 230000002745 absorbent Effects 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 10
- 239000002808 molecular sieve Substances 0.000 claims description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 10
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 235000021357 Behenic acid Nutrition 0.000 claims description 4
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 4
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940116226 behenic acid Drugs 0.000 claims description 4
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 3
- 238000001179 sorption measurement Methods 0.000 claims description 3
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 34
- 239000002994 raw material Substances 0.000 abstract description 8
- 239000004032 superbase Substances 0.000 abstract description 6
- 150000007525 superbases Chemical class 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 5
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000012530 fluid Substances 0.000 description 8
- 239000000499 gel Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910052593 corundum Inorganic materials 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 229910001845 yogo sapphire Inorganic materials 0.000 description 3
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- UAUDZVJPLUQNMU-UHFFFAOYSA-N Erucasaeureamid Natural products CCCCCCCCC=CCCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- 239000006004 Quartz sand Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 229960004025 sodium salicylate Drugs 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OOFAEFCMEHZNGP-UHFFFAOYSA-N 1-n',1-n'-dimethylpropane-1,1-diamine Chemical compound CCC(N)N(C)C OOFAEFCMEHZNGP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the technical field of chemical synthesis preparation, and particularly relates to fatty amide propyl dimethyl tertiary amine and a preparation method and application thereof. The method comprises the steps of carrying out amidation reaction on fatty acid and N, N-dimethyl-1, 3-propane diamine, and carrying out reduced pressure distillation to obtain the fatty acid amide propyl dimethyl tertiary amine; the method comprises the following steps of preparing fatty amide propyl dimethyl tertiary amine, and performing amidation reaction on fatty amide propyl dimethyl tertiary amine by using a catalyst of boric acid and/or stannous octoate. According to the method, on the premise that solid superbase is not used as a catalyst, the conversion rate of the prepared fatty amidopropyl dimethyl tertiary amine is high, the toxicity of the catalyst such as superbase and the like and the corrosion to equipment are avoided, the large-scale production is facilitated, the energy is saved, the environment is protected, the preparation process flow is simple, meanwhile, the reutilization of partial raw materials can be realized, and the cost of the raw materials is reduced.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis preparation, and particularly relates to fatty amide propyl dimethyl tertiary amine and a preparation method and application thereof.
Background
The fatty amide propyl dimethyl tertiary amine is an important chemical raw material, can be used as an ore flotation agent, an asphalt emulsifier, a paper waterproofing agent, a foaming agent, a thickening agent, an oil field chemical auxiliary agent and the like, is also an intermediate and a raw material for producing amine oxide, hydrochloride, betaine and the like, is widely applied to the industries of daily chemicals, washing, fracturing acidification, foaming and the like, and has wide industrial application value and large market demand.
The traditional method for preparing fatty amide propyl dimethyl tertiary amine is to synthesize fatty amide propyl dimethyl tertiary amine by taking fatty acid and N, N-dimethyl propane diamine as raw materials through condensation reaction, and sodium ethoxide, sodium hydroxide and the like are commonly used as catalysts, but the catalysts have low catalytic efficiency, are difficult to recover and are not environment-friendly. For example, chinese patent document CN107573254B discloses a method for preparing a fatty amide dimethyl tertiary amine compound by using solid superbase, which uses solid superbase as a catalyst, can corrode enamel equipment, and is not suitable for large-scale industrial production. Meanwhile, in the traditional process, the reaction temperature is over-high, generally 160-.
Further, chinese patent document CN106588688A discloses a method for purifying fatty amide propyl dimethyl tertiary amine, in which excessive 3-dimethylaminopropylamine needs to be removed by nitrogen purge, and the 3-dimethylaminopropylamine is strongly irritating to human mucous membranes, respiratory tracts and skin, and thus the exhaust gas needs to be treated.
Disclosure of Invention
Therefore, the invention aims to overcome the defects that in the prior art, a super-strong base catalyst is required to be adopted when the fatty amidopropyl dimethyl tertiary amine is prepared, the scale production is not facilitated, the reaction condition requirement is strict, the process is complex, the conversion rate of the fatty amidopropyl dimethyl tertiary amine is low, and the like, so that the fatty amidopropyl dimethyl tertiary amine and the preparation method and application thereof are provided.
Therefore, the invention provides the following technical scheme.
The invention provides a preparation method of fatty amide propyl dimethyl tertiary amine, which comprises the following steps,
fatty acid and N, N-dimethyl-1, 3-propane diamine are subjected to amidation reaction and reduced pressure distillation to obtain fatty amide propyl dimethyl tertiary amine;
wherein, the process of preparing the fatty amide propyl dimethyl tertiary amine also comprises the step of water diversion;
the catalyst for amidation reaction is boric acid and/or stannous octoate.
Further, the step of dividing water is carried out in a mode of absorbing a water absorbing agent;
the water absorbent is 4A molecular sieve and/or anhydrous sodium sulfate.
The water diversion step specifically comprises the following steps: the water diversion device is communicated with the reactor, a water absorbent is placed in the water diversion device, water generated in the amidation reaction can form water vapor, part of N, N-dimethyl-1, 3-propanediamine in the reactor can also form steam, the steam and the water vapor form mixed steam, the mixed steam is condensed to form mixed liquid, the mixed liquid enters the water diversion device, the water absorbent absorbs water in the mixed liquid to obtain relatively pure N, N-dimethyl-1, 3-propanediamine, the water diversion step is realized, and the N, N-dimethyl-1, 3-propanediamine can be recycled to the reaction kettle for reuse.
The mass ratio of the catalyst to the fatty acid is (0.01-0.5): 100.
the molar ratio of the fatty acid to the N, N-dimethyl-1, 3-propanediamine is 1: (1-1.1).
The temperature of the amidation reaction is 100-150 ℃, and the time is 4-6 h.
The fatty acid is C18-C22 series fatty acid.
The fatty acid is at least one of oleic acid, fatty acid, behenic acid and erucic acid.
The reduced pressure distillation temperature is 90-120 deg.C, the time is 30-60min, and the vacuum degree is 0.5-10 kPa.
The invention also provides the fatty amide propyl dimethyl tertiary amine prepared by the method.
In addition, the invention also provides application of the fatty amide propyl dimethyl tertiary amine prepared by the method or the fatty amide propyl dimethyl tertiary amine in the field of oilfield fracturing production increase.
The technical scheme of the invention has the following advantages:
1. the invention provides a preparation method of fatty amide propyl dimethyl tertiary amine, which comprises the steps of carrying out amidation reaction on fatty acid and N, N-dimethyl-1, 3 propane diamine, and carrying out reduced pressure distillation to obtain the fatty amide propyl dimethyl tertiary amine; the method comprises the following steps of preparing fatty amide propyl dimethyl tertiary amine, and performing amidation reaction on fatty amide propyl dimethyl tertiary amine by using a catalyst of boric acid and/or stannous octoate. According to the method, on the premise that solid superbase is not used as a catalyst, the conversion rate of the prepared fatty amidopropyl dimethyl tertiary amine is high, the toxicity of the catalyst such as superbase and the like and the corrosion to equipment are avoided, the large-scale production is facilitated, the energy is saved, the environment is protected, the preparation process flow is simple, meanwhile, the reutilization of partial raw materials can be realized, and the cost of the raw materials is reduced. The invention also comprises a water diversion step in the process of preparing the fatty amide propyl dimethyl tertiary amine, wherein water in the mixed solution is removed, the amidation reaction can be promoted to be carried out, the conversion rate of the fatty amide propyl dimethyl tertiary amine is improved, pure N, N-dimethyl-1, 3 propane diamine can be obtained after water diversion, the adding amount of the raw material of the N, N-dimethyl-1, 3 propane diamine is reduced, the production cost is reduced, the problem that the wastewater containing the N, N-dimethyl-1, 3 propane diamine and water is separated by adopting a reduced pressure distillation mode in the prior art is avoided, increase the production cost and consume large energy.
According to the invention, boric acid and/or stannous octoate are/is used as a catalyst, so that the problem that the equipment is corroded by using super-strong solid alkali in the prior art can be avoided, and the obtained product does not contain suspended matters and does not need to be filtered.
The fatty amide propyl dimethyl tertiary amine prepared by the invention can be used in the industries of daily chemicals, washing, oil production and displacement by petroleum, flotation and the like, and can also be used as a raw material for preparing betaine.
2. According to the preparation method of the fatty amide propyl dimethyl tertiary amine, the 4A molecular sieve and/or the anhydrous sodium sulfate are/is used as the water absorbent, water generated in the process of preparing the fatty amide propyl dimethyl tertiary amine is removed, the conversion rate is favorably improved, pure N, N-dimethyl-1, 3 propane diamine can be obtained after water separation treatment, the N, N-dimethyl-1, 3 propane diamine is recycled, the production cost is not increased, and the environmental pollution is not caused. In the prior art, water is generated when the fatty amide propyl dimethyl tertiary amine is prepared, and the N, N-dimethyl-1, 3 propane diamine is mutually dissolved with the water to form waste water, so that the N, N-dimethyl-1, 3 propane diamine needs to be recovered from the waste water.
Furthermore, the 4A molecular sieve and/or anhydrous sodium sulfate are/is used as the water absorbent, water with the diameter smaller than 4A can be absorbed, the selective adsorption performance on water is higher than that of other water absorbents, and the water absorbent can be reused after being treated after being saturated in adsorption.
3. According to the preparation method of the fatty acid amide propyl dimethyl tertiary amine, when the fatty acid amide propyl dimethyl tertiary amine is prepared, the mode of slightly excessive N, N-dimethyl-1, 3 propane diamine is controlled, and the molar ratio of fatty acid to the N, N-dimethyl-1, 3 propane diamine is 1: (1-1.1), the cost for removing the N, N-dimethyl-1, 3-propane diamine in the later period is low, and the conversion rate can be ensured.
By controlling the reduced pressure distillation, unreacted N, N-dimethyl-1, 3-propane diamine and a small amount of water in the product can be distilled off, and the purity of the product is improved.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
Example 1
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1412.5kg of oleic acid (5.0kmol) and 536.5kg of N, N-dimethyl-1, 3-propanediamine (5.25kmol) are added into a reactor, 0.283kg of boric acid catalyst is added after uniform stirring, the reaction is heated to 143 ℃ for amidation reaction for 5h, then the temperature is reduced to 110 ℃, the vacuum degree is controlled to be 0.8kPa, and the reduced pressure distillation time is 35min, thus obtaining the oleamide propyl dimethyl tertiary amine. The reactor is communicated with a water diversion device, a 4A molecular sieve and anhydrous sodium sulfate are arranged in the water diversion device, steam can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed by the steam and the mixed steam, mixed liquor is obtained after the mixed steam is condensed and enters the water diversion device to be diverted, a water absorbent absorbs water in the mixed liquor, the water diversion step is realized in the process of preparing fatty amide propyl dimethyl tertiary amine, pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion, and the pure N, N-dimethyl-1, 3-propanediamine can be introduced into the reactor again to be reused.
Example 2
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1422.5kg of stearic acid (5.0kmol) and 526.3kg of N, N-dimethyl-1, 3-propanediamine (5.15kmol) are added into a reactor, 0.426kg of stannous octoate catalyst is added after the mixture is stirred uniformly, the mixture is heated to 135 ℃ for amidation reaction for 4 hours, then the temperature is reduced to 100 ℃, the vacuum degree is controlled to be 1.0kPa, and the reduced pressure distillation time is 35min, thus obtaining the stearamidopropyl dimethyl tertiary amine. The reactor is communicated with a water diversion device, anhydrous sodium sulfate is arranged in the water diversion device, water vapor can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed with the water vapor, mixed steam is condensed to obtain mixed liquor, the mixed liquor enters the water diversion device to be diverted, a water absorbent absorbs water in the mixed liquor, the water diversion step is realized in the process of preparing the fatty amide propyl dimethyl tertiary amine, and pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion and can be introduced into the reactor again for reuse.
Example 3
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1702.9kg of behenic acid (5.0kmol) and 551.9kg of N, N-dimethyl-1, 3-propanediamine (5.40kmol) are added into a reactor, 0.341kg of stannous octoate and 0.341kg of boric acid are added after uniform stirring, the temperature is heated to 110 ℃ for amidation reaction, the reaction time is 6 hours, then the temperature is reduced to 100 ℃, the vacuum degree is controlled to be 5.0kPa, and the reduced pressure distillation time is 45 minutes, so that the behenamidopropyl dimethyl tertiary amine is obtained. The reactor is communicated with a water diversion device, a 4A molecular sieve and anhydrous sodium sulfate are arranged in the water diversion device, steam can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed by the steam and the mixed steam, mixed liquor is obtained after the mixed steam is condensed and enters the water diversion device to be diverted, a water absorbent absorbs water in the mixed liquor, the water diversion step is realized in the process of preparing fatty amide propyl dimethyl tertiary amine, pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion, and the pure N, N-dimethyl-1, 3-propanediamine can be introduced into the reactor again to be reused.
Example 4
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1692.85kg of erucic acid (5.0kmol) and 562.1kg of N, N-dimethyl-1, 3-propanediamine (5.50kmol) are added into a reactor, after being uniformly stirred, 3.386kg of stannous octoate and 3.386kg of boric acid are added, the mixture is heated to 100 ℃ for amidation reaction, the reaction time is 5 hours, then the temperature is reduced to 120 ℃, the vacuum degree is controlled to be 7.0kPa, and the reduced pressure distillation time is 30 minutes, thus obtaining the erucamide propyl dimethyl tertiary amine. The reactor is communicated with a water diversion device, a 4A molecular sieve is arranged in the water diversion device, water vapor can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed with the water vapor, mixed steam is condensed to obtain mixed liquid, the mixed liquid enters the water diversion device for water diversion, a water absorbent absorbs water in the mixed liquid, the water diversion step is realized in the process of preparing fatty amide propyl dimethyl tertiary amine, pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion, and the pure N, N-dimethyl-1, 3-propanediamine can be introduced into the reactor again for reuse.
Example 5
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1422.5kg of stearic acid (5.0kmol) and 526.3kg of N, N-dimethyl-1, 3-propanediamine (5.15kmol) are added into a reactor, 0.426kg of stannous octoate catalyst is added after the mixture is stirred uniformly, the mixture is heated to 95 ℃ for amidation reaction for 4 hours, then the temperature is reduced to 100 ℃, the vacuum degree is controlled to be 1.0kPa, and the reduced pressure distillation time is 35min, so that the stearamidopropyl dimethyl tertiary amine is obtained. The reactor is communicated with a water diversion device, anhydrous sodium sulfate is arranged in the water diversion device, water vapor can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed with the water vapor, mixed steam is condensed to obtain mixed liquor, the mixed liquor enters the water diversion device to be diverted, a water absorbent absorbs water in the mixed liquor, the water diversion step is realized in the process of preparing the fatty amide propyl dimethyl tertiary amine, and pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion and can be introduced into the reactor again for reuse.
Example 6
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1702.9kg of behenic acid (5.0kmol) and 551.9kg of N, N-dimethyl-1, 3-propanediamine (5.40kmol) are added into a reactor, 0.341kg of stannous octoate and 0.341kg of boric acid are added after uniform stirring, the temperature is heated to 110 ℃ for amidation reaction, the reaction time is 6 hours, then the temperature is reduced to 85 ℃, the vacuum degree is controlled to be 5.0kPa, and the reduced pressure distillation time is 45 minutes, so that the behenamidopropyl dimethyl tertiary amine is obtained. The reactor is communicated with a water diversion device, a 4A molecular sieve and anhydrous sodium sulfate are arranged in the water diversion device, steam can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed by the steam and the mixed steam, mixed liquor is obtained after the mixed steam is condensed and enters the water diversion device to be diverted, a water absorbent absorbs water in the mixed liquor, the water diversion step is realized in the process of preparing fatty amide propyl dimethyl tertiary amine, pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion, and the pure N, N-dimethyl-1, 3-propanediamine can be introduced into the reactor again to be reused.
Example 7
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1692.85kg of erucic acid (5.0kmol) and 562.1kg of N, N-dimethyl-1, 3-propanediamine (5.50kmol) are added into a reactor, after being uniformly stirred, 3.386kg of stannous octoate and 3.386kg of boric acid are added, the mixture is heated to 100 ℃ for amidation reaction, the reaction time is 5 hours, then the temperature is reduced to 120 ℃, the vacuum degree is controlled to be 7.0kPa, and the reduced pressure distillation time is 20 minutes, thus obtaining the erucamide propyl dimethyl tertiary amine. The reactor is communicated with a water diversion device, a 4A molecular sieve is arranged in the water diversion device, water vapor can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed with the water vapor, mixed steam is condensed to obtain mixed liquid, the mixed liquid enters the water diversion device for water diversion, a water absorbent absorbs water in the mixed liquid, the water diversion step is realized in the process of preparing fatty amide propyl dimethyl tertiary amine, pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion, and the pure N, N-dimethyl-1, 3-propanediamine can be introduced into the reactor again for reuse.
Example 8
This example provides a method for preparing fatty amidopropyl dimethyl tertiary amine, which comprises the following steps,
1412.5kg of oleic acid (5.0kmol) and 505.9kg of N, N-dimethyl-1, 3-propanediamine (4.90kmol) are added into a reactor, 0.283kg of boric acid catalyst is added after uniform stirring, the reaction is heated to 143 ℃ for amidation reaction for 5h, then the temperature is reduced to 110 ℃, the vacuum degree is controlled to be 0.8kPa, and the reduced pressure distillation time is 35min, so that the oleamide propyl dimethyl tertiary amine is obtained. The reactor is communicated with a water diversion device, a 4A molecular sieve and anhydrous sodium sulfate are arranged in the water diversion device, steam can be generated in the reaction process, part of N, N-dimethyl-1, 3-propanediamine forms steam, mixed steam is formed by the steam and the mixed steam, mixed liquor is obtained after the mixed steam is condensed and enters the water diversion device to be diverted, a water absorbent absorbs water in the mixed liquor, the water diversion step is realized in the process of preparing fatty amide propyl dimethyl tertiary amine, pure N, N-dimethyl-1, 3-propanediamine is obtained after water diversion, and the pure N, N-dimethyl-1, 3-propanediamine can be introduced into the reactor again to be reused.
Comparative example 1
This comparative example provides a process for the preparation of fatty amidopropyl dimethyl tertiary amine without water diversion during the reaction, the reactor is not connected to a water diversion device, and the other conditions are the same as in example 1.
Comparative example 2
This comparative example provides a process for the preparation of fatty amidopropyl dimethyl tertiary amine without water absorbent in the water diversion apparatus, otherwise the conditions were the same as in example 1.
Comparative example 3
The comparative example provides a preparation method of fatty amide propyl dimethyl tertiary amine, and the catalyst is KF/Al2O3The amount used was 1% by mass of oleic acid, namely 14.13kg, and the other conditions were the same as in example 1.
Comparative example 4
This comparative example provides a method for preparing fatty amidopropyl dimethyl tertiary amine without adding boric acid catalyst, otherwise the conditions are the same as example 1.
Comparative example 5
This comparative example provides a method for preparing fatty acid amide propyl dimethyl tertiary amine, the catalyst is sodium borohydride, the dosage is 0.5% of the mass of oleic acid, 7.06kg, and other conditions are the same as example 1. The product obtained in this comparative example had suspended matter floating therein and required filtration before use.
Test examples
The test examples provide the performance tests and test results of the fatty amidopropyl dimethyl tertiary amines prepared in examples 1-8 and comparative examples 1-5, the test methods are as follows, and the test results are shown in Table 1.
The method for testing the tertiary amine value in the fatty amide propyl dimethyl tertiary amine comprises the following steps: reference is made to the method specified in 5.3 of GB/T15045-.
The method for testing the free acid in the fatty amide propyl dimethyl tertiary amine comprises the following steps: weighing 50ml of absolute ethanol, adding 1-3 drops of phenolphthalein indicator, dropwise adding an ethanol solution containing KOH for titration until the color changes, keeping the color unchanged for 15s, then adding 0.5-1g of fatty amide propyl dimethyl tertiary amine sample, oscillating to uniformly dissolve the sample, dropwise adding an ethanol solution containing KOH for titration until the color changes, keeping the color unchanged for 15s, recording the volume of the ethanol solution containing KOH consumed at the moment, and calculating according to formula 1 to obtain the content of free acid;
wherein, A is the content of free acid, and the unit is%;
c is the molar concentration of KOH in the ethanol solution containing KOH, the unit is mol/L, and the molar concentration of the ethanol solution containing KOH in the test example is 0.1 mol/L;
v is the volume of the ethanol solution containing KOH consumed, and the unit is ml;
m is the relative molecular weight of the fatty acid, and the unit is g/mol;
m is the weight of the fatty amide propyl dimethyl tertiary amine, and the unit is g.
The conversion of fatty amidopropyl dimethyl tertiary amine was calculated according to formula 2,
wherein:
r is the conversion rate of fatty amide propyl dimethyl tertiary amine;
a is the content of free fatty acid, and the unit is%;
mgeneral assemblyThe total weight of the fatty acid and the N, N-dimethyl-1, 3-propane diamine is kg;
macid(s)Is the total weight of fatty acids in kg.
Method for testing color of fatty amide propyl dimethyl tertiary amine: to 100ml of a 25% ethanol solution was added fatty amidopropyl dimethyl tertiary amine, and the color was measured according to the method specified in GB/T3143.
The application of fatty acid amide propyl dimethyl tertiary amine in the field of oilfield fracturing production increase is characterized in that 50g of fatty acid amide propyl dimethyl tertiary amine is slowly added into 1000g of mixed solution (containing 30g of p-toluenesulfonic acid, 15g of potassium chloride, 8g of sodium salicylate, 400g of isopropanol and 547g of water) while stirring, the water and the isopropanol are uniformly mixed, then the p-toluenesulfonic acid, the potassium chloride and the sodium salicylate are added, and the mixed solution is obtained after uniform mixing, so that fracturing fluid gel is obtained. Taking 50g of fracturing fluid gel, adopting an RS6000 rheometer, and performing fracturing at 120 ℃ for 170s-1The shear viscosity of the fracturing fluid gel is tested under the condition, the test time is 120min, and the shear viscosity is more than 50mPa & s, which indicates that the fracturing fluid gel meets the requirements of a petroleum industry standard SY/T6376; the fatty acid amidopropyl dimethyl tertiary amine prepared in each example and comparative example was made into a fracturing fluid jelly according to the above method, and the shear viscosity at 120min was measured according to the above method, and the results are shown in table 1.
TABLE 1 Performance test results for fatty amidopropyldimethyl Tertiary amine
From the results of Table 1, comparative example 1, which did not undergo the treatment for dividing water, resulted in a decrease in conversion rate, and a large amount of fatty acid did not participate in the reaction, resulting in an excessively high content of free acid and a decrease in tertiary amine value, as compared to example 1. Comparative example 2 although the conversion was significantly improved compared to comparative example 1 with the water diversion apparatus, the conversion of fatty amidopropyldimethyl tertiary amine was also significantly lower compared to example 1 due to the absence of the water-absorbing agent.
Comparative example 3 adopts super strong alkali catalyst, and KF/Al2O3As a catalyst, although the conversion rate was improved as compared with comparative examples 1-2, the conversion rate of comparative example 3 was still low, part of fatty acids were not reacted, and the free acid value was high as compared with example 1; while comparative example 3 added Al2O3Since the reaction environment of the fatty acid and the N, N-dimethyl-1, 3-propanediamine is a strong alkaline environment, Al is caused2O3And decomposing to obtain a turbid product with high color.
In comparison with example 1, no catalyst was added in comparative example 4, so that the reaction rate of comparative example 4 was decreased under the same reaction conditions, so that the conversion rate was decreased under the same conditions; the free acid content of comparative example 4 increased due to the large amount of unreacted fatty acid.
In the comparative example 5, sodium borohydride is added as a catalyst, and sodium borohydride is a reducing agent, so that the influence of dissolved oxygen on the color and the color of the product can be effectively solved, the color of the product is lighter, compared with the example 1, the color is lighter, and suspended matters float in the obtained product and can be used after being filtered.
The experimental results of example 2 and example 5 show that example 2 can improve the conversion rate of the product and reduce the free acid in the product by optimizing the temperature of the amidation reaction. The experimental results of example 3 and example 6 show that N, N-dimethyl-1, 3-propanediamine in the product can be further removed by optimizing the temperature of reduced pressure distillation, and in example 6, partial N, N-dimethyl-1, 3-propanediamine is not distilled off and the tertiary amine value is higher due to insufficient reduced pressure distillation time; the experimental results of example 4 and example 7 show that example 4 can further remove N, N-dimethyl-1, 3-propanediamine from the product by optimizing the time of distillation under reduced pressure. The experimental results of example 1 and example 8 demonstrate that example 1 can convert fatty acids into tertiary amines, increase the conversion, and decrease the content of free acids by optimizing the amounts of fatty acids and N, N-dimethyl-1, 3 propanediamine.
According to the results in the table 1, the fatty amide propyl dimethyl tertiary amine prepared by the invention has better shear viscosity, and is suitable for the field of oilfield fracturing yield increase. When the fracturing fluid gel is used for oil field fracturing and production increase, the fracturing fluid gel can be mixed with proppants such as quartz sand and the like and pumped into a shaft. If the shearing viscosity is too low (less than 50mPa · s), the problem that the quartz sand quickly sinks to block a well mouth is easy to occur. According to the invention, parameters such as amidation reaction temperature, fatty acid-N, N-dimethyl-1, 3-propane diamine molar ratio, reduced pressure distillation temperature, reduced pressure distillation time and the like are optimized, so that the shear viscosity of the fracturing fluid gel can be further improved, and the method is more suitable for being applied to the field of oilfield fracturing yield increase.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the spirit or scope of the invention.
Claims (10)
1. A method for preparing fatty amide propyl dimethyl tertiary amine is characterized by comprising the following steps,
fatty acid and N, N-dimethyl-1, 3-propane diamine are subjected to amidation reaction and reduced pressure distillation to obtain fatty amide propyl dimethyl tertiary amine;
wherein, the process of preparing the fatty amide propyl dimethyl tertiary amine also comprises the step of water diversion;
the catalyst for amidation reaction is boric acid and/or stannous octoate.
2. The production method according to claim 1, wherein the water-dividing step is performed by means of adsorption of a water-absorbing agent;
the water absorbent is 4A molecular sieve and/or anhydrous sodium sulfate.
3. The production method according to claim 1 or 2, characterized in that the mass ratio of the catalyst to the fatty acid is (0.01-0.5): 100.
4. the process according to any one of claims 1 to 3, wherein the molar ratio of the fatty acid to the N, N-dimethyl-1, 3-propanediamine is from 1: (1-1.1).
5. The process according to any one of claims 1 to 4, wherein the temperature of the amidation reaction is 100 ℃ and 150 ℃ for 4 to 6 hours.
6. The method according to any one of claims 1 to 5, wherein the fatty acid is a C18-C22 series fatty acid.
7. The method according to any one of claims 1 to 6, wherein the fatty acid is at least one of oleic acid, fatty acid, behenic acid and erucic acid.
8. The production process according to any one of claims 1 to 7, wherein the reduced pressure distillation is carried out at a temperature of 90 to 120 ℃ for 30 to 60 minutes under a vacuum of 0.5 to 10 kPa.
9. Fatty amidopropyl dimethyl tertiary amine prepared by the method of any one of claims 1-8.
10. The fatty amide propyl dimethyl tertiary amine prepared by the preparation method of any one of claims 1 to 8 or the fatty amide propyl dimethyl tertiary amine of claim 9 is applied to the field of oilfield fracturing stimulation.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115678531A (en) * | 2022-11-02 | 2023-02-03 | 咸阳川庆鑫源工程技术有限公司 | Instant salt-resistant surfactant fracturing fluid, preparation method thereof and fluid preparation device |
CN116003282A (en) * | 2022-12-31 | 2023-04-25 | 杭州瑞思新材料有限公司 | Preparation method of antistatic agent |
Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6737446B1 (en) * | 2003-01-03 | 2004-05-18 | Air Products And Chemicals, Inc. | Tertiary amino alkyl amide catalysts for improving the physical properties of polyurethane foams |
CN102603549A (en) * | 2012-02-28 | 2012-07-25 | 四川西普化工股份有限公司 | Method for synthesizing erucamide propyl betaine |
CN103524370A (en) * | 2013-09-27 | 2014-01-22 | 中国石油天然气股份有限公司 | Fatty acid mixture amide propyl betaine and preparation method thereof |
CN104059620A (en) * | 2014-07-09 | 2014-09-24 | 哈尔滨工业大学 | Water-in-oil type polyamide emulsifier for drilling fluid and synthetizing method thereof |
CN104211616A (en) * | 2013-06-05 | 2014-12-17 | 中国石油化工股份有限公司 | Preparation method for antioxidant |
CN105348441A (en) * | 2015-12-10 | 2016-02-24 | 李准 | Production process of ultralow-concentration clean thickening agent fracturing fluid for petroleum oil-gas well |
CN106278922A (en) * | 2016-08-15 | 2017-01-04 | 广州天赐高新材料股份有限公司 | A kind of preparation method of fatty acid amide propyl tertiary amine |
CN106496059A (en) * | 2016-08-31 | 2017-03-15 | 四川花语精细化工有限公司 | The process of free acid in a kind of reduction glycine betaine |
CN106588688A (en) * | 2016-11-30 | 2017-04-26 | 江南大学 | Fatty acid amide propyl dimethylamine refining method |
CN106800520A (en) * | 2016-12-12 | 2017-06-06 | 广州大学 | A kind of betaine type amphoteric surfac-tant and preparation method thereof |
CN107142099A (en) * | 2017-05-19 | 2017-09-08 | 中国石油大学(华东) | A kind of CO of reusable edible2Response type clean fracturing fluid |
CN107573254A (en) * | 2017-10-10 | 2018-01-12 | 河南省科学院高新技术研究中心 | A kind of method that fatty acid amide dimethyl tertiary amine class compound is prepared using solid super base |
CN110283091A (en) * | 2019-08-08 | 2019-09-27 | 淄博鲁瑞精细化工有限公司 | The synthetic method of amides defoaming agent |
CN111302965A (en) * | 2020-04-01 | 2020-06-19 | 唐山华熠实业股份有限公司 | Novel preparation process of naphthol |
CN112957998A (en) * | 2021-02-08 | 2021-06-15 | 张家港格瑞特化学有限公司 | Preparation method of surfactant composition |
-
2021
- 2021-07-27 CN CN202110852707.5A patent/CN113651709A/en active Pending
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6737446B1 (en) * | 2003-01-03 | 2004-05-18 | Air Products And Chemicals, Inc. | Tertiary amino alkyl amide catalysts for improving the physical properties of polyurethane foams |
CN102603549A (en) * | 2012-02-28 | 2012-07-25 | 四川西普化工股份有限公司 | Method for synthesizing erucamide propyl betaine |
CN104211616A (en) * | 2013-06-05 | 2014-12-17 | 中国石油化工股份有限公司 | Preparation method for antioxidant |
CN103524370A (en) * | 2013-09-27 | 2014-01-22 | 中国石油天然气股份有限公司 | Fatty acid mixture amide propyl betaine and preparation method thereof |
CN104059620A (en) * | 2014-07-09 | 2014-09-24 | 哈尔滨工业大学 | Water-in-oil type polyamide emulsifier for drilling fluid and synthetizing method thereof |
CN105348441A (en) * | 2015-12-10 | 2016-02-24 | 李准 | Production process of ultralow-concentration clean thickening agent fracturing fluid for petroleum oil-gas well |
CN106278922A (en) * | 2016-08-15 | 2017-01-04 | 广州天赐高新材料股份有限公司 | A kind of preparation method of fatty acid amide propyl tertiary amine |
CN106496059A (en) * | 2016-08-31 | 2017-03-15 | 四川花语精细化工有限公司 | The process of free acid in a kind of reduction glycine betaine |
CN106588688A (en) * | 2016-11-30 | 2017-04-26 | 江南大学 | Fatty acid amide propyl dimethylamine refining method |
CN106800520A (en) * | 2016-12-12 | 2017-06-06 | 广州大学 | A kind of betaine type amphoteric surfac-tant and preparation method thereof |
CN107142099A (en) * | 2017-05-19 | 2017-09-08 | 中国石油大学(华东) | A kind of CO of reusable edible2Response type clean fracturing fluid |
CN107573254A (en) * | 2017-10-10 | 2018-01-12 | 河南省科学院高新技术研究中心 | A kind of method that fatty acid amide dimethyl tertiary amine class compound is prepared using solid super base |
CN110283091A (en) * | 2019-08-08 | 2019-09-27 | 淄博鲁瑞精细化工有限公司 | The synthetic method of amides defoaming agent |
CN111302965A (en) * | 2020-04-01 | 2020-06-19 | 唐山华熠实业股份有限公司 | Novel preparation process of naphthol |
CN112957998A (en) * | 2021-02-08 | 2021-06-15 | 张家港格瑞特化学有限公司 | Preparation method of surfactant composition |
Non-Patent Citations (1)
Title |
---|
马夏坪等: "硼酸催化合成N,N-二甲基-N′-月桂酰基-1,3-丙二胺及其同系物", 《化学世界》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115678531A (en) * | 2022-11-02 | 2023-02-03 | 咸阳川庆鑫源工程技术有限公司 | Instant salt-resistant surfactant fracturing fluid, preparation method thereof and fluid preparation device |
CN116003282A (en) * | 2022-12-31 | 2023-04-25 | 杭州瑞思新材料有限公司 | Preparation method of antistatic agent |
CN116003282B (en) * | 2022-12-31 | 2024-03-05 | 杭州瑞思新材料有限公司 | Preparation method of antistatic agent |
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