CN106800520A - A kind of betaine type amphoteric surfac-tant and preparation method thereof - Google Patents
A kind of betaine type amphoteric surfac-tant and preparation method thereof Download PDFInfo
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- CN106800520A CN106800520A CN201611140819.3A CN201611140819A CN106800520A CN 106800520 A CN106800520 A CN 106800520A CN 201611140819 A CN201611140819 A CN 201611140819A CN 106800520 A CN106800520 A CN 106800520A
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- type amphoteric
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- 239000002280 amphoteric surfactant Substances 0.000 title claims abstract description 37
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 title claims abstract description 33
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 title claims abstract description 33
- 229960003237 betaine Drugs 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 76
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000011938 amidation process Methods 0.000 claims abstract description 32
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 25
- 239000002808 molecular sieve Substances 0.000 claims abstract description 24
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 24
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 propyl dimethyl tertiary amine Chemical class 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- 125000003368 amide group Chemical group 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- 230000008859 change Effects 0.000 abstract description 3
- 239000006260 foam Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 64
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 40
- 235000021314 Palmitic acid Nutrition 0.000 description 20
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000012043 crude product Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 238000010792 warming Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- 238000002390 rotary evaporation Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 208000012839 conversion disease Diseases 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 235000021360 Myristic acid Nutrition 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 0 C*C(*CCC[N+](C)*)O Chemical compound C*C(*CCC[N+](C)*)O 0.000 description 2
- 239000001293 FEMA 3089 Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- QEALYLRSRQDCRA-UHFFFAOYSA-N myristamide Chemical compound CCCCCCCCCCCCCC(N)=O QEALYLRSRQDCRA-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- LNFURSPIYHWENY-UHFFFAOYSA-N C[N+](C)(CC(O)=O)=C Chemical compound C[N+](C)(CC(O)=O)=C LNFURSPIYHWENY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PRPAGESBURMWTI-UHFFFAOYSA-N [C].[F] Chemical group [C].[F] PRPAGESBURMWTI-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- 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
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of betaine type amphoteric surfac-tant and preparation method thereof, the preparation method of the betaine type amphoteric surfac-tant is comprised the following steps：1）Amidation process：Natural oil resin acid and 3 DIMAPAs carry out amidation process in the presence of catalyst, and obtain alkylamide propyl dimethyl tertiary amine in time except the water of dereaction generation using 4A molecular sieves；2）Quaternary ammonium reaction：Alkylamide propyl dimethyl tertiary amine carries out quaternary ammonium reaction in a solvent with sodium chloroacetate, obtains betaine type amphoteric surfac-tant.Contain amido link in amphoteric surfactant group of the invention, change the performance of molecule, with more preferable foam stability, moderate performance, its emulsifiability is substantially better than empgen BB surfactant.Preparation method process is simple of the invention, low production cost, raw material green natural, and the water produced during amidation process is absorbed by 4A molecular sieves, improve yield.
Description
Technical field
The present invention relates to a kind of betaine type amphoteric surfac-tant and preparation method thereof.
Background technology
Amphoteric surfactant refers in same molecular structure while existing by bridge chain (hydrocarbon chain, carbon fluorine chain etc.) even
The surfactant of one or more the positive and negative charge-sites (or dipole center) for connecing, its biodegradability is good, low toxicity, anti-
Electrostatic.Amphoteric surfactant appears in the thirties in 20th century earliest, and application is progressively developed later, and China is in both sexes table
Research and development in terms of the activating agent of face are started late, and there is a big difference compared with other developed countries for kind and yield.
Domestic surfactant based on anionic surfactant and nonionic surfactant, this two classes surface
Activating agent pollutes the environment, it is difficult to biodegradable.Alkylamide propyl-betaine is that a kind of new and effective amphoteric surface lives
Property agent, containing amide group and quaternary amines, with moderate performance, decontamination is strong, frothing capacity is good, conditioning performance is superior etc.
Advantage, is widely used in articles for washing, particularly shampoo, hair cream etc. in recent years.At present, personal care articles industry alkane
The annual consumption of base amide betaine amphoteric surfactant is about ten tens of thousands of tons, wide market.
The preparation process of alkylamide propyl-betaine is broadly divided into following two step：1) amidation process：With aliphatic acid and
3- DIMAPAs prepare alkylamide propyl dimethyl tertiary amine for raw material；2) quaternary ammonium reaction：With alkylamide propyl two
Methyl tertiary amine and sodium chloroacetate are raw material, and water and isopropanol prepare alkylamide propyl-betaine as reaction dissolvent.Mainly deposit
In problems with：1) acid number of amidation process is difficult to reduce, so that yield is relatively low, production cost is higher；2) mostly with mixing
Fatty acid is raw materials for production, but this kind of fatty acid contains more impurity, and property is unstable, and it is production also to have with fatty acid methyl esters
Raw material, but further increase production cost；3) purifying technique is fairly simple, and the Product Activity content of material for obtaining is low.
The content of the invention
It is an object of the invention to provide a kind of betaine type amphoteric surfac-tant and preparation method thereof.
The technical solution used in the present invention is：
A kind of betaine type amphoteric surfac-tant, its structural formula is：
Wherein n is 12 or 14 or 16.
The preparation method of above-mentioned betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：By the fusing of natural oil resin acid, 3- DIMAPAs are added, fully mixed, add catalyst
Amidation process is carried out, 4A molecular sieves are added after 5~7h of reaction, continue to react, unreacted 3- diformazans are removed after completion of the reaction
Amido propylamine and natural oil resin acid, obtain alkylamide propyl dimethyl tertiary amine；
2) quaternary ammonium reaction：Alkylamide propyl dimethyl tertiary amine and sodium chloroacetate are added into reactor, chloroethene is added water to
The dissolving of sour sodium is complete, adds isopropanol, and regulation pH value carries out quaternary ammonium reaction to 7~8, remove after completion of the reaction isopropanol,
Water and unreacted sodium chloroacetate, obtain betaine type amphoteric surfac-tant.
Step 1) described in the structural formula of natural oil resin acid be：Wherein n be 12 or 14 or
16。
Step 1) described in catalyst be KOH, NaOH, NaF, CH3One kind in ONa, addition is natural oil resin acid matter
The 0.3%~0.7% of amount.
Step 1) described in natural oil resin acid, 3- DIMAPAs mol ratio be 1：(1.05~1.08).
Step 1) described in natural oil resin acid, 4A molecular sieves mass ratio be 1：(0.33~0.46).
Step 1) described in amidation process reaction temperature be 160~180 DEG C, the reaction time be 9~11 hours.
Step 2) described in alkylamide propyl dimethyl tertiary amine, sodium chloroacetate mol ratio be 1：(1.05~1.15).
Step 2) described in water, isopropanol volume ratio be (1.5~2)：1.
Step 2) described in quaternary ammonium reaction reaction temperature be 80~95 DEG C, the reaction time be 4~6 hours.
The present invention relates to reaction it is as follows：
1) amidation process：
2) quaternary ammonium reaction：
The beneficial effects of the invention are as follows：
1) contain amido link in amphoteric surfactant group of the invention, the performance of molecule is changed, with more preferable
Foam stability, moderate performance, its emulsifiability is substantially better than empgen BB surfactant；
2) preparation method process is simple of the invention, low production cost, selected reaction raw materials are natural oil resin acid, its
Source is wide, green safety, degradable, and the water produced during amidation process is absorbed by 4A molecular sieves, can be effective
Promote reaction is carried out to positive direction, improves yield.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of betaine type amphoteric surfac-tant prepared by embodiment 1.
Fig. 2 is the proton nmr spectra of betaine type amphoteric surfac-tant prepared by embodiment 1.
Fig. 3 is the surface tension test result figure of betaine type amphoteric surfac-tant prepared by embodiment 1.
Fig. 4 is the solubilising test result figure of the betaine type amphoteric surfac-tant to benzene of the preparation of embodiment 1.
Fig. 5 is influence test result figure of the 4A molecular sieves to amidation process conversion ratio.
Specific embodiment
A kind of betaine type amphoteric surfac-tant, its structural formula is：
Wherein n is 12 or 14 or 16.
The preparation method of above-mentioned betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：By the fusing of natural oil resin acid, 3- DIMAPAs are added, fully mixed, add catalyst
Carry out
Amidation process, 4A molecular sieves are added after 5~7h of reaction, continue to react, and are removed after completion of the reaction unreacted
3- DIMAPAs and natural oil resin acid, obtain alkylamide propyl dimethyl tertiary amine；
2) quaternary ammonium reaction：Alkylamide propyl dimethyl tertiary amine and sodium chloroacetate are added into reactor, chloroethene is added water to
Sour sodium is molten
Solution is complete, adds isopropanol, and regulation pH value carries out quaternary ammonium reaction, removes after completion of the reaction different to 7~8
Propyl alcohol, water and unreacted sodium chloroacetate, obtain betaine type amphoteric surfac-tant.
Preferably, step 1) described in the structural formula of natural oil resin acid be：Wherein n is
12 or 14 or 16.
Preferably, step 1) described in catalyst be KOH, NaOH, NaF, CH3One kind in ONa, addition is natural oil
The 0.3%~0.7% of resin acid quality.
Preferably, step 1) described in natural oil resin acid, 3- DIMAPAs mol ratio be 1：(1.05~1.08).
Preferably, step 1) described in natural oil resin acid, 4A molecular sieves mass ratio be 1：(0.33~0.46).
Preferably, step 1) described in the reaction temperature of amidation process be 160~180 DEG C, the reaction time is 9~11 small
When.
Preferably, step 2) described in alkylamide propyl dimethyl tertiary amine, sodium chloroacetate mol ratio be 1：(1.05~
1.15)。
Preferably, step 2) described in water, isopropanol volume ratio be (1.5~2)：1.
Preferably, step 2) described in quaternary ammonium reaction reaction temperature be 80~95 DEG C, the reaction time be 4~6 hours.
The present invention is made further explanation and description with reference to specific embodiment.
Embodiment 1：
A kind of preparation method of betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：The palmitic acid of 25.6475g is added in the there-necked flask equipped with reflux condenser, is warming up to
80 DEG C cause that palmitic acid slowly melts, then 3- DIMAPAs (palmitic acid and the 3- dimethylamine of 10.728g are added dropwise while stirring
The mol ratio of base propylamine is 1:1.05), 30min is dripped off, and adds the KOH of 0.177g as catalyst, is warming up to 160 DEG C, is entered
Row amidation process, adds the 4A molecular sieves of 10g after reaction 6h, continue to react 5h, and first vacuum distillation after completion of the reaction removes thick
Unreacted 3- DIMAPAs and water byproduct in product, then with the Na of mass fraction 1%2CO3Solution washing removes not anti-
The palmitic acid answered, obtains palmitamide propyl-dimethyl tertiary amine, and yield is 93.42%；
2) quaternary ammonium reaction：The palmitamide dimethylamine of 34.06g is added in the there-necked flask equipped with reflux condenser
(palmitamide propyl-dimethyl tertiary amine is 1 with the mol ratio of sodium chloroacetate to the sodium chloroacetate of base tertiary amine and 13.40g:1.15), then
Adding the water of 30.5g makes sodium chloroacetate dissolve completely just, adds the isopropanol of 15.25g, and pH is between 7~8 for regulation, rises
Warm to 80 DEG C carry out quaternary ammonium reaction, and amine value of once dissociating is determined every a hour, and after reaction 6h, conversion ratio is not further added by,
Stop reaction, obtain crude product, rotary evaporation removes the isopropyl alcohol and water in crude product, and the isopropanol for adding 3 times of volumes is molten
Solution filtering, removes unreacted sodium chloroacetate, and last rotary evaporation reclaims isopropanol, obtains palmitamide CAB, i.e.,
Betaine type amphoteric surfac-tant of the invention, yield is 95.32%.
The infrared spectrogram of palmitamide CAB manufactured in the present embodiment is as shown in figure 1, its proton nmr spectra
As shown in Figure 2 (500MHz, DMSO).
As shown in Figure 1：3311.58cm-1It is the stretching vibration absworption peak of hydrogen bound to nitrogen N-H to locate；2918.13cm-1、
2850.62cm-1And 1467.74cm-1It is the stretching vibration absworption peak of C-H bond C-H to locate；1641.33cm-1Locate for amido link-
The characteristic absorption peak of CONH-；1552.61cm-1Locate the antisymmetric stretching vibration absworption peak for carboxylate, and 1398.31cm-1Place
It is its symmetrical stretching vibration absworption peak；1232.44cm-1It is the vibration absorption peak of carbonnitrogen bond-C-N- to locate；721.33cm-1Locate for-
(CH2)n- rocking vibration absworption peak.
As shown in Figure 2：δ=7.75-7.72 (s, 1H ,-CONH-), δ=4.43-4.09 (s, 2H, N+-CH2COO-), δ=
3.37-3.34 (s, 6H, CH3-N+-CH3), δ=3.11-2.94 (s, 4H ,-NH-CH2-CH2-CH2-N+), δ=2.17-2.12
(s, 2H ,-CH2-CO-), δ=2.09-2.08 (m, 2H ,-CH2-CH2-CH2-N+), δ=1.47-1.44 (s, 2H ,-CH2-CH2-
CONH-), δ=1.24-1.19 (s, 22H ,-(CH2)11-), δ=1.12-1.03 (s, 2H ,-CH2-CH3), δ=0.85 (s, 3H ,-
CH3)。
Complex chart 1 and Fig. 2 understand：Palmitamide CAB product impurity prepared by above-mentioned technological process is few, purity
It is higher.
Embodiment 2：
A kind of preparation method of betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：The myristic acid of 22.84g is added in the there-necked flask equipped with reflux condenser, is warming up to
80 DEG C cause that myristic acid slowly melts, then 3- DIMAPAs (myristic acid and the 3- bis- of 10.73g are added dropwise while stirring
The mol ratio of methylamino propylamine is 1:1.05), 30min is dripped off, and adds the NaOH of 0.17g as catalyst, is warming up to 160
DEG C, amidation process is carried out, the 4A molecular sieves of 10g are added after reaction 6h, continue to react 5h, first vacuum distillation after completion of the reaction is removed
Go unreacted 3- DIMAPAs and water byproduct in crude product, then with the Na of mass fraction 1%2CO3Solution washing is removed
Unreacted myristic acid, obtains myristamide propyl-dimethyl tertiary amine, and yield is 92.31%；
2) quaternary ammonium reaction：The myristamide propyl group two of 31.26g is added in the there-necked flask equipped with reflux condenser
(myristamide propyl-dimethyl tertiary amine is 1 with the mol ratio of sodium chloroacetate to the sodium chloroacetate of methyl tertiary amine and 13.40g:
1.15), adding the water of 30.50g makes sodium chloroacetate dissolving is complete just, adds the isopropanol of 15.25g, regulation pH 7~
Between 8, being warming up to 80 DEG C carries out quaternary ammonium reaction, and amine value of once dissociating is determined every a hour, and after reaction 6h, conversion ratio is not
It is further added by, stops reaction, obtain crude product, rotary evaporation removes the isopropyl alcohol and water in crude product, adds the different of 3 times of volumes
Propyl alcohol dissolution filter, removes unreacted sodium chloroacetate, and last rotary evaporation reclaims isopropanol, obtains myristamide propyl group sweet
Dish alkali, i.e., betaine type amphoteric surfac-tant of the invention, yield is 94.86%.
Embodiment 3：
A kind of preparation method of betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：The palmitic acid of 25.64g is added in the there-necked flask equipped with reflux condenser, 80 are warming up to
DEG C cause that palmitic acid slowly melts, then 3- DIMAPAs (palmitic acid and the 3- dimethylamine of 11.1169g are added dropwise while stirring
The mol ratio of base propylamine is 1:1.08), 30min is dripped off, and adds the NaF of 0.18g as catalyst, is warming up to 160 DEG C, is carried out
Amidation process, adds the 4A molecular sieves of 10g after reaction 6h, continue to react 5h, and first vacuum distillation after completion of the reaction removes thick producing
Unreacted 3- DIMAPAs and water byproduct in thing, then with the Na of mass fraction 1%2CO3Solution washing removes unreacted
Palmitic acid, obtain palmitamide propyl-dimethyl tertiary amine, yield is 89.46%；
2) quaternary ammonium reaction：The palmitamide dimethylamine of 34.16g is added in the there-necked flask equipped with reflux condenser
(palmitamide propyl-dimethyl tertiary amine is 1 with the mol ratio of sodium chloroacetate to the sodium chloroacetate of base tertiary amine and 12.40g:1.06), then
Adding the water of 31g makes sodium chloroacetate dissolve completely just, adds the isopropanol of 15.25g, and pH is between 7~8 for regulation, heats up
Quaternary ammonium reaction is carried out to 80 DEG C, amine value of once dissociating is determined every a hour, reaction continues 6h, and conversion ratio is not further added by,
Stop reaction, obtain crude product, rotary evaporation removes the isopropyl alcohol and water in crude product, and the isopropanol for adding 3 times of volumes is molten
Solution filtering, removes unreacted sodium chloroacetate, and last rotary evaporation reclaims isopropanol, obtains palmitamide CAB, i.e.,
Betaine type amphoteric surfac-tant of the invention, yield is 76.22%.
Embodiment 4：
A kind of preparation method of betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：The palmitic acid of 25.67g is added in the there-necked flask equipped with reflux condenser, 80 are warming up to
DEG C cause that palmitic acid slowly melts, then 3- DIMAPAs (palmitic acid and the 3- dimethylamino of 11.43g are added dropwise while stirring
The mol ratio of propylamine is 1:1.06), 30min is dripped off, and adds the CH of 0.190g3ONa is warming up to 160 DEG C as catalyst, enters
Row amidation process, adds the 4A molecular sieves of 10g after reaction 6h, continue to react 5h, and first vacuum distillation after completion of the reaction removes thick
Unreacted 3- DIMAPAs and water byproduct in product, then with the Na of mass fraction 1%2CO3Solution washing removes not anti-
The palmitic acid answered, obtains palmitamide propyl-dimethyl tertiary amine, and yield is 89.60%；
2) quaternary ammonium reaction：The palmitamide dimethylamine of 34.01g is added in the there-necked flask equipped with reflux condenser
(palmitamide propyl-dimethyl tertiary amine is 1 with the mol ratio of sodium chloroacetate to the sodium chloroacetate of base tertiary amine and 12.2g:1.05), then
Adding the water of 30g makes sodium chloroacetate dissolve completely just, adds the isopropanol of 11.80g, and pH is between 7~8 for regulation, heats up
Quaternary ammonium reaction is carried out to 95 DEG C, amine value of once dissociating is determined every a hour, after reaction 6h, conversion ratio is not further added by, and stops
Only react, obtain crude product, rotary evaporation removes the isopropyl alcohol and water in crude product, add 3 times of isopropanol dissolvings of volume
Filtering, removes unreacted sodium chloroacetate, and last rotary evaporation reclaims isopropanol, obtains palmitamide CAB, i.e., originally
The betaine type amphoteric surfac-tant of invention, yield is 84.31%.
Embodiment 5：
A kind of preparation method of betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：The palmitic acid of 25.63g is added in the there-necked flask equipped with reflux condenser, 80 are warming up to
DEG C cause that palmitic acid slowly melts, then 3- DIMAPAs (palmitic acid and the 3- dimethylamino of 10.78g are added dropwise while stirring
The mol ratio of propylamine is 1:1.05), 30min is dripped off, and adds the NaOH of 0.190g as catalyst, is warming up to 160 DEG C, is carried out
Amidation process, adds the 4A molecular sieves of 10g after reaction 6h, continue to react 5h, and first vacuum distillation after completion of the reaction removes thick producing
Unreacted 3- DIMAPAs and water byproduct in thing, then with the Na of mass fraction 1%2CO3Solution washing removes unreacted
Palmitic acid, obtain palmitamide propyl-dimethyl tertiary amine, yield is 89.31%；
2) quaternary ammonium reaction：The palmitamide dimethylamine of 34.39g is added in the there-necked flask equipped with reflux condenser
(palmitamide propyl-dimethyl tertiary amine is 1 with the mol ratio of sodium chloroacetate to the sodium chloroacetate of base tertiary amine and 13.08g:1.11), then
Adding the water of 27g makes sodium chloroacetate dissolve completely just, adds the isopropanol of 16.12g, and pH is between 7~8 for regulation, heats up
Quaternary ammonium reaction is carried out to 85 DEG C, amine value of once dissociating is determined every a hour, after reaction 6h, conversion ratio is not further added by, and stops
Only react, obtain crude product, rotary evaporation removes the isopropyl alcohol and water in crude product, add 3 times of isopropanol dissolvings of volume
Filtering, removes unreacted sodium chloroacetate, and last rotary evaporation reclaims isopropanol, obtains palmitamide CAB, i.e., originally
The betaine type amphoteric surfac-tant of invention, yield is 88.28%.
Embodiment 6：
A kind of preparation method of betaine type amphoteric surfac-tant is comprised the following steps：
1) amidation process：The palmitic acid of 25.65g is added in the there-necked flask equipped with reflux condenser, 80 are warming up to
DEG C cause that palmitic acid slowly melts, then 3- DIMAPAs (palmitic acid and the 3- dimethylamino of 10.83g are added dropwise while stirring
The mol ratio of propylamine is 1:1.06), 30min is dripped off, and adds the KOH of 0.19g as catalyst, is warming up to 160 DEG C, carries out acyl
Aminating reaction, adds the 4A molecular sieves of 10g after reaction 6h, continue to react 5h, and first vacuum distillation after completion of the reaction removes crude product
In unreacted 3- DIMAPAs and water byproduct, then with the Na of mass fraction 1%2CO3Solution washing removes unreacted
Palmitic acid, obtains palmitamide propyl-dimethyl tertiary amine, and yield is 89.31%；
2) quaternary ammonium reaction：The palmitamide dimethylamine of 34.39g is added in the there-necked flask equipped with reflux condenser
(palmitamide propyl-dimethyl tertiary amine is 1 with the mol ratio of sodium chloroacetate to the sodium chloroacetate of base tertiary amine and 12.71g:1.10), then
Adding the water of 27g makes sodium chloroacetate dissolve completely just, adds the isopropanol of 16.12g, and pH is between 7~8 for regulation, heats up
Quaternary ammonium reaction is carried out to 85 DEG C, amine value of once dissociating is determined every a hour, after reaction 6h, conversion ratio is not further added by, and stops
Only react, obtain crude product, rotary evaporation removes the isopropyl alcohol and water in crude product, add 3 times of isopropanol dissolvings of volume
Filtering, removes unreacted sodium chloroacetate, and last rotary evaporation reclaims isopropanol, obtains palmitamide CAB, i.e., originally
The betaine type amphoteric surfac-tant of invention, yield is 84.62%.
Test case：
1) surface tension test
Surface tension test is carried out to palmitamide CAB prepared by embodiment 1 at 24 DEG C, test result is such as
Shown in Fig. 3.
As shown in Figure 3：With being continuously increased for surfactant concentration, the surface tension of solution is gradually reduced, until going out
The change of surface tension tends towards stability after existing flex point, and the critical micelle concentration cmc for thus obtaining palmitamide CAB is
1.12×10-4Mol/L, corresponding γcmcIt is 31.63mN/m, the performance with the surface tension for preferably reducing water, this benefit
In the chain hydrophobic alkyl that palmitamide CAB possesses.
2) solubilising to benzene is tested
The solubilising test to benzene, test result such as Fig. 4 institutes are carried out to palmitamide CAB prepared by embodiment 1
Show.
As shown in Figure 4：The solubilized limit A of palmitamide CABPAPB=0.498ml, is calculated palmitamide
The solubilising power X=4980ml/mol of CAB, because the palmitamide CAB of synthesis has chain hydrophobic end,
So the aggregation number of the surfactant is than larger, so that the solubilizing amount for being solubilized into the non-polar hydrocarbon of micelle inner core increases
Plus, with preferable characteristic of solubilizing.
3) emulsifiability test
The palmitamide CAB and empgen BB prepared to embodiment 1 carry out emulsifiability test, survey
Test result is as shown in table 1：
The emulsifiability of the palmitamide CAB of table 1 and empgen BB in different oil phases
As shown in Table 1：Palmitamide CAB prepared by embodiment 1 is suitable to the emulsifying capacity size of different oil phases
Sequence is as follows：Benzene ＞ turpentine oil ＞ atoleine ＞ tetrafluoroethene, and its emulsifiability to benzene, turpentine oil and tetrafluoroethene is bright
It is aobvious to be better than empgen BB.It is primarily due to draw in alkylamide propyl-betaine type surfactant group of the invention
Amide group is entered, has changed the performance of molecule, made it have more preferable foam stability, mildness, increasing has been played in formula
Plus the effect of viscosity, compatibility and solubility property can be substantially improved, expand and contain in its range of application, and the long-chain of synthetic product
The ability of 16 atomicities and the surface tension with good reduction water so that its emulsion process median surface film strength increases
By force, emulsibility is also improved therewith.
4) influence of the 4A molecular sieves to amidation process conversion ratio
At 160 DEG C, acid is 1 with amine mol ratio:1.05, ω(KOH)Under conditions of=0.5%, amidation process process is contrasted
Middle to add and without 4A molecular sieves, reaction conversion ratio changes with time, and test result is as shown in Figure 5.
As shown in Figure 5：Before 5h, addition and be all with time rapid growth without 4A molecular sieves reaction conversion ratio
, the reaction conversion ratio of that group after 5h without 4A molecular sieves is basicly stable, raises not substantially, but addition 4A molecular sieves
Reaction conversion ratio of that group continue to raise, final reaction conversion ratio is apparently higher than that group without 4A molecular sieves, reaction
What is carried out is more thorough, and being primarily due to 4A molecular sieves can absorb the water of amidation process generation, so as to promote reaction forward
Carry out, reaction conversion ratio is also improved therewith.Therefore, selection adds 4A molecular sieves more to close after amidation process carries out 5~7h
It is suitable.
Above-described embodiment is the present invention preferably implementation method, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from Spirit Essence of the invention and the change, modification, replacement made under principle, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (10)
1. a kind of betaine type amphoteric surfac-tant, it is characterised in that：Its structural formula is：
Wherein n is 12 or 14 or 16.
2. a kind of preparation method of betaine type amphoteric surfac-tant, it is characterised in that：Comprise the following steps：
1) amidation process：By the fusing of natural oil resin acid, 3- DIMAPAs are added, fully mixed, add catalyst to carry out
Amidation process, 4A molecular sieves are added after 5~7h of reaction, continue to react, and unreacted 3- dimethylamino is removed after completion of the reaction
Propylamine and natural oil resin acid, obtain alkylamide propyl dimethyl tertiary amine；
2) quaternary ammonium reaction：Alkylamide propyl dimethyl tertiary amine and sodium chloroacetate are added into reactor, sodium chloroacetate is added water to
Dissolving is complete, adds isopropanol, and regulation pH value carries out quaternary ammonium reaction to 7~8, remove after completion of the reaction isopropanol, water and
Unreacted sodium chloroacetate, obtains betaine type amphoteric surfac-tant.
3. preparation method according to claim 2, it is characterised in that：Step 1) described in natural oil resin acid structural formula
For：
Wherein n is 12 or 14 or 16.
4. preparation method according to claim 2, it is characterised in that：Step 1) described in catalyst for KOH, NaOH,
NaF、CH3One kind in ONa, addition is the 0.3%~0.7% of natural oil resin acid quality.
5. preparation method according to claim 2, it is characterised in that：Step 1) described in natural oil resin acid, 3- dimethylamine
The mol ratio of base propylamine is 1：(1.05~1.08).
6. preparation method according to claim 2, it is characterised in that：Step 1) described in natural oil resin acid, 4A molecular sieves
Mass ratio be 1：(0.33~0.46).
7. preparation method according to claim 2, it is characterised in that：Step 1) described in amidation process reaction temperature
It it is 160~180 DEG C, the reaction time is 9~11 hours.
8. preparation method according to claim 2, it is characterised in that：Step 2) described in alkylamide propyl dimethyl uncle
Amine, the mol ratio of sodium chloroacetate are 1：(1.05~1.15).
9. preparation method according to claim 2, it is characterised in that：Step 2) described in water, the volume ratio of isopropanol be
(1.5~2)：1.
10. preparation method according to claim 2, it is characterised in that：Step 2) described in quaternary ammonium reaction reaction temperature
It is 80~95 DEG C to spend, and the reaction time is 4~6 hours.
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| CN109943004A (en) * | 2019-02-25 | 2019-06-28 | 郭迎庆 | A kind of preparation method of butadiene rubber composite material |
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| CN117164472A (en) * | 2023-08-16 | 2023-12-05 | 碳中能源科技(北京)有限公司 | Viscoelastic amphoteric surfactant and high-temperature-resistant fracturing fluid prepared from viscoelastic amphoteric surfactant |
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