CN101654421A - Synthesis method of cocoamidopropyl-2-hydroxyl-3-sulfopropyl betaine - Google Patents
Synthesis method of cocoamidopropyl-2-hydroxyl-3-sulfopropyl betaine Download PDFInfo
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- CN101654421A CN101654421A CN200910102017A CN200910102017A CN101654421A CN 101654421 A CN101654421 A CN 101654421A CN 200910102017 A CN200910102017 A CN 200910102017A CN 200910102017 A CN200910102017 A CN 200910102017A CN 101654421 A CN101654421 A CN 101654421A
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Abstract
The invention discloses a synthesis method of cocoamidopropyl-2-hydroxyl-3-sulfopropyl betaine, which adopts coconut oil fatty acid, N,N-dimethyl propane diamine, epoxy chloropropane and sodium bisulfite anhydrous as raw materials. The synthesis method comprises the following specific steps of carrying out amidation reaction on coconut oil fatty acid and N,N-dimethyl propane diamine to generate intermediate cocoamide; then carrying out addition reaction on epoxy chloropropane and sodium bisulfite anhydrous to generate intermediate sodium propylsulfonate; and finally carrying out quaternizationreaction on the produced intermediate cocoamide and the intermediate sodium propylsulfonate under the existence of a catalyst so as to generate the target product, namely, the cocoamidopropyl-2-hydroxyl-3-sulfopropyl betaine. The product of the synthesis method has good hard water resistance, conditioning and antistatic property, is stable in the wide range of pH value, is not influenced in acid-base medium, is stable in an electrolyte system and is degradable and non-toxic.
Description
Technical field
The present invention relates to the synthetic method of a kind of novel daily-use chemical industry formulation monomer cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine, belong to the synthesis technical field of zwitterionics in the organic chemistry.
Background technology
Cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine is colourless to weak yellow liquid, water-soluble, can with various tensio-active agent compatibilities, can reduce the pungency of other tensio-active agents, foam is abundant and fine and smooth and not influenced by the pH value, and stability in hard water is good, tool conditioning property and static resistance.Stable in wide ph range, unaffected in acid-alkali medium, stable in electrolyte system.Degradable is nontoxic.Cooperate with sulfated lauryl alcohol and α-Xi Jihuangsuanyan, foam and viscosity are good.Good dispersion of calcium soap is arranged.Can be used as suds booster, washing composition, cloud point inhibitor, hydrotropic agent etc.Be suitable for preparing the senior shampoo of mild, bathe with goods, amendment, skin cleaner, skin-protecting agent infant articles for washing and family expenses and dish washing detergent.
Synthetic method about cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine there is no report both at home and abroad, just occurs in some external daily necessities prescriptions, as U.S. Lonzaine company
CS, French Rhodia company
CBS, U.S. Stepan company
CS-50.
Summary of the invention
In order to address the above problem, the object of the present invention is to provide a kind of novel daily-use chemical industry formulation monomer---the synthetic method of zwitterionics cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine product.Product stability in hard water of the present invention is good, tool conditioning property and static resistance; Stable in wide ph range, unaffected in acid-alkali medium, stable in electrolyte system; And degradable is nontoxic.
For reaching above-mentioned purpose, the present invention adopts following technical scheme,
The synthetic method of a kind of cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine, with commercially available coco-nut oil fatty acid, N, N-dimethylated propyl diethylenetriamine, epoxy chloropropane, anhydrous sodium sodium pyrosulfate are raw material, concrete steps are: (1) with coco-nut oil fatty acid and N, N-dimethylated propyl diethylenetriamine amidate action generates the intermediate coconut oleoyl amine; Reaction equation is:
(RCO is a cocoyl)
(2) again epoxy chloropropane and the addition reaction of anhydrous sodium sodium pyrosulfate are generated intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium; Reaction equation is:
(3) quaterisation takes place in the intermediate hydroxypropyl azochlorosulfonate acid sodium that makes of intermediate coconut oleoyl amine that at last step (1) is made and step (1) in the presence of catalyzer, generates target product cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine; Reaction equation is:
(RCO is a cocoyl).
Described coco-nut oil fatty acid and N, the mass ratio of N-dimethylated propyl diethylenetriamine are 1: 0.49～0.78.
Described coco-nut oil fatty acid and N, the mass ratio of N-dimethylated propyl diethylenetriamine is preferably 1: 0.59.
Described coco-nut oil fatty acid and N, the amidate action of N-dimethylated propyl diethylenetriamine carries out in two stages: the fs, coco-nut oil fatty acid and N, salt-forming reaction takes place at 60～110 ℃ in the N-dimethylated propyl diethylenetriamine, generates ammonium salt, and the reaction times is 1.0～4.0h; Subordinate phase, ammonium salt generate the intermediate coconut oleoyl amine 140～200 ℃ of dehydrations, and be reflected under the negative pressure and carry out, reaction pressure 20～200Pa, the reaction times is 1.0～4.0h.
The mass ratio of described epoxy chloropropane and anhydrous sodium sodium pyrosulfate is 1: 1.12～1.46; Temperature of reaction can be 40～90 ℃, and the reaction times is 3.0～8.0h.
The mass ratio of described epoxy chloropropane and anhydrous sodium sodium pyrosulfate is preferably 1: 1.29.
The mass ratio of described intermediate coconut oleoyl amine and intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium is 1: 0.65～0.70; Temperature of reaction can be 60～90 ℃, and the reaction times is 2.0～8.0h.
The mass ratio of described intermediate coconut oleoyl amine and intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium is preferably 1: 0.67.
Described intermediate coconut oleoyl amine and intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium catalyst for reaction can be a kind of in sodium hydroxide, the potassium hydroxide, and the catalyzer add-on is 1～10% of intermediate coconut oleoyl amine and an intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium total mass.
The molecular weight of described product cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine is 429 (molecular weight of cocoyl RCO is in 208).
The invention has the beneficial effects as follows: the present invention is a kind of novel household chemicals raw material---cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine, and mainly as suds booster, washing composition, cloud point inhibitor, hydrotropic agent etc.Be suitable for preparing the senior shampoo of mild, bathe with goods, amendment, skin cleaner, skin-protecting agent infant articles for washing and family expenses and dish washing detergent.Can with various tensio-active agent compatibilities, can reduce the pungency of other tensio-active agents, foam is abundant and fine and smooth and not influenced by pH value, stability in hard water is good, tool is nursed one's health property and static resistance.Stable in wide ph range, unaffected in acid-alkali medium, stable in electrolyte system.Degradable is nontoxic.Cooperate with sulfated lauryl alcohol and α-Xi Jihuangsuanyan, foam and viscosity are good.Good dispersion of calcium soap is arranged.
Embodiment
Embodiment 1
Ability case step 1: add 500kg coco-nut oil fatty acid (purchasing in Shandong Boxing Huarun Grease Chemical Co., Ltd) in reactor, be stirred and heated to 85～90 ℃, begin to drip 246kgN, the N-dimethylated propyl diethylenetriamine adds insulation reaction 4.0h.At pressure 20Pa, 200 ℃ of insulation reaction 4.0h of temperature, obtain the intermediate coconut oleoyl amine then.
Step 2: add the 222kg epoxy chloropropane in reactor, be stirred and heated to 85～90 ℃, beginning adds 250kg anhydrous sodium sodium pyrosulfate in batches, adds insulation reaction 8.0h, obtains intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium.
Step 3: in reactor, add 667kg intermediate coconut oleoyl amine, be heated to 85～90 ℃, add 11kg potassium hydroxide, beginning adds 434kg intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium in batches, add insulation reaction 8.0h, obtain target product cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine, molecular weight is 429.
Embodiment 2
Present embodiment step 1: add 500kg coco-nut oil fatty acid (purchasing in Shandong Boxing Huarun Grease Chemical Co., Ltd) in reactor, be stirred and heated to 60～62 ℃, begin to drip 295kgN, the N-dimethylated propyl diethylenetriamine adds insulation reaction 2.0h.At pressure 100Pa, 160 ℃ of insulation reaction 3.0h of temperature, obtain the intermediate coconut oleoyl amine then.
Step 2: add the 222kg epoxy chloropropane in reactor, be stirred and heated to 60～65 ℃, beginning adds 287kg anhydrous sodium sodium pyrosulfate in batches, adds insulation reaction 5.0h, obtains intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium.
Step 3: in reactor, add 667kg intermediate coconut oleoyl amine, be heated to 80～85 ℃, add 46kg potassium hydroxide, beginning adds 447kg intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium in batches, add insulation reaction 4.0h, obtain target product cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine, molecular weight is 429.
Embodiment 3
Present embodiment step 1: add 500kg coco-nut oil fatty acid (purchasing in Shandong Boxing Huarun Grease Chemical Co., Ltd) in reactor, be stirred and heated to 105～110 ℃, begin to drip 390kg N, the N-dimethylated propyl diethylenetriamine adds insulation reaction 1.0h.At pressure 200Pa, 140 ℃ of insulation reaction 1.0h of temperature, obtain the intermediate coconut oleoyl amine then.
Step 2: add the 222kg epoxy chloropropane in reactor, be stirred and heated to 40～45 ℃, beginning adds 324kg anhydrous sodium sodium pyrosulfate in batches, adds insulation reaction 3.0h, obtains intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium.
Step 3: in reactor, add 667kg intermediate coconut oleoyl amine, be heated to 60～65 ℃, add 113kg sodium hydroxide, beginning adds 467kg intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium in batches, add insulation reaction 2.0h, obtain target product cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine, molecular weight is 429.
Claims (10)
1, the synthetic method of a kind of cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine, with coco-nut oil fatty acid, N, N-dimethylated propyl diethylenetriamine, epoxy chloropropane, anhydrous sodium sodium pyrosulfate are raw material, it is characterized in that concrete steps are:
(1) with coco-nut oil fatty acid and N, N-dimethylated propyl diethylenetriamine amidate action generates the intermediate coconut oleoyl amine; Reaction equation is:
(RCO is a cocoyl)
(2) again epoxy chloropropane and the addition reaction of anhydrous sodium sodium pyrosulfate are generated intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium; Reaction equation is:
(3) quaterisation takes place in the intermediate hydroxypropyl azochlorosulfonate acid sodium that makes of intermediate coconut oleoyl amine that at last step (1) is made and step (1) in the presence of catalyzer, generates target product cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine; Reaction equation is:
(RCO is a cocoyl).
2, the synthetic method of cocamidopropyl propyl amide as claimed in claim 1-2-hydroxyl-3-sulfopropyl betaine, it is characterized in that: described coco-nut oil fatty acid and N, the mass ratio of N-dimethylated propyl diethylenetriamine are 1: 0.49～0.78.
3, the synthetic method of cocamidopropyl propyl amide as claimed in claim 2-2-hydroxyl-3-sulfopropyl betaine, it is characterized in that: described coco-nut oil fatty acid and N, the mass ratio of N-dimethylated propyl diethylenetriamine are 1: 0.59.
4, the synthetic method of cocamidopropyl propyl amide as claimed in claim 1-2-hydroxyl-3-sulfopropyl betaine, it is characterized in that: described coco-nut oil fatty acid and N, the amidate action of N-dimethylated propyl diethylenetriamine carries out in two stages: the fs, coco-nut oil fatty acid and N, salt-forming reaction takes place at 60～110 ℃ in the N-dimethylated propyl diethylenetriamine, generate ammonium salt, the reaction times is 1.0～4.0h; Subordinate phase, ammonium salt generate the intermediate coconut oleoyl amine 140～200 ℃ of dehydrations, and be reflected under the negative pressure and carry out, reaction pressure 20～200Pa, the reaction times is 1.0～4.0h.
5, the synthetic method of cocamidopropyl propyl amide as claimed in claim 1-2-hydroxyl-3-sulfopropyl betaine, it is characterized in that: the mass ratio of described epoxy chloropropane and anhydrous sodium sodium pyrosulfate is 1: 1.12～1.46; Temperature of reaction can be 40～90 ℃, and the reaction times can be 3.0～8.0.
6, the synthetic method of cocamidopropyl propyl amide as claimed in claim 5-2-hydroxyl-3-sulfopropyl betaine, it is characterized in that: the mass ratio of described epoxy chloropropane and anhydrous sodium sodium pyrosulfate is 1: 1.29.
7, the synthetic method of cocamidopropyl propyl amide as claimed in claim 1-2-hydroxyl-3-sulfopropyl betaine is characterized in that: the mass ratio of described intermediate coconut oleoyl amine and intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium is 1: 0.65～0.70; Temperature of reaction can be 60～90 ℃, and the reaction times can be 2.0～8.0h.
8, the synthetic method of cocamidopropyl propyl amide as claimed in claim 7-2-hydroxyl-3-sulfopropyl betaine is characterized in that: the mass ratio of described intermediate coconut oleoyl amine and intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium is 1: 0.67.
9, the synthetic method of cocamidopropyl propyl amide as claimed in claim 1-2-hydroxyl-3-sulfopropyl betaine, it is characterized in that: described intermediate coconut oleoyl amine and intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium catalyst for reaction are a kind of in sodium hydroxide, the potassium hydroxide, and the catalyzer add-on is 1～10% of intermediate coconut oleoyl amine and an intermediate chlorine hydroxypropyl azochlorosulfonate acid sodium total mass.
10, the synthetic method of cocamidopropyl propyl amide as claimed in claim 9-2-hydroxyl-3-sulfopropyl betaine is characterized in that: the molecular weight of described product cocamidopropyl propyl amide-2-hydroxyl-3-sulfopropyl betaine is 429.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101856600A (en) * | 2010-06-25 | 2010-10-13 | 西北大学 | Amphoteric ionic Gemini surfactant and synthetic method thereof |
| CN102503864A (en) * | 2011-10-28 | 2012-06-20 | 广州花语精细化工有限公司 | Method for synthesizing low-salt fatty acid amide propyl hydroxy sulfobetaine |
| CN102863948A (en) * | 2012-10-14 | 2013-01-09 | 东北石油大学 | Hydroxysulfobetaine amphoteric surfactant for flooding and preparation method of hydroxysulfobetaine amphoteric surfactant |
| CN106701052A (en) * | 2017-01-16 | 2017-05-24 | 中国石油大学(华东) | Microbial-chemical composite oil displacement agent and preparation method and application thereof |
| CN108948342A (en) * | 2018-08-07 | 2018-12-07 | 江苏四新界面剂科技有限公司 | A kind of preparation method of the chain of oxyethylene group containing poly amphoteric surfactant |
| CN110845372A (en) * | 2019-11-26 | 2020-02-28 | 陕西科技大学 | Multiolefin hook type surfactant gel fracturing fluid and preparation and gel breaking methods thereof |
| CN110950785A (en) * | 2019-11-26 | 2020-04-03 | 陕西科技大学 | Twin-tail hook type viscoelastic surfactant gel, preparation method thereof and gel removing method |
| CN112956478A (en) * | 2021-02-19 | 2021-06-15 | 广西汇丰生物科技有限公司 | Synergistic composition and application thereof in pesticide preparation of aqueous suspension |
| CN112980419A (en) * | 2019-12-13 | 2021-06-18 | 中国石油天然气股份有限公司 | Thick oil foaming agent and preparation method and application thereof |
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2009
- 2009-08-27 CN CN200910102017A patent/CN101654421A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101856600A (en) * | 2010-06-25 | 2010-10-13 | 西北大学 | Amphoteric ionic Gemini surfactant and synthetic method thereof |
| CN102503864A (en) * | 2011-10-28 | 2012-06-20 | 广州花语精细化工有限公司 | Method for synthesizing low-salt fatty acid amide propyl hydroxy sulfobetaine |
| CN102863948A (en) * | 2012-10-14 | 2013-01-09 | 东北石油大学 | Hydroxysulfobetaine amphoteric surfactant for flooding and preparation method of hydroxysulfobetaine amphoteric surfactant |
| CN106701052A (en) * | 2017-01-16 | 2017-05-24 | 中国石油大学(华东) | Microbial-chemical composite oil displacement agent and preparation method and application thereof |
| CN106701052B (en) * | 2017-01-16 | 2019-02-19 | 中国石油大学(华东) | A kind of microbial-chemical compound oil displacement agent and its preparation method and application |
| CN108948342A (en) * | 2018-08-07 | 2018-12-07 | 江苏四新界面剂科技有限公司 | A kind of preparation method of the chain of oxyethylene group containing poly amphoteric surfactant |
| CN110845372A (en) * | 2019-11-26 | 2020-02-28 | 陕西科技大学 | Multiolefin hook type surfactant gel fracturing fluid and preparation and gel breaking methods thereof |
| CN110950785A (en) * | 2019-11-26 | 2020-04-03 | 陕西科技大学 | Twin-tail hook type viscoelastic surfactant gel, preparation method thereof and gel removing method |
| CN110950785B (en) * | 2019-11-26 | 2021-10-01 | 陕西科技大学 | Twin-tail hook type viscoelastic surfactant gel, preparation method thereof and gel removing method |
| CN112980419A (en) * | 2019-12-13 | 2021-06-18 | 中国石油天然气股份有限公司 | Thick oil foaming agent and preparation method and application thereof |
| CN112980419B (en) * | 2019-12-13 | 2023-01-10 | 中国石油天然气股份有限公司 | Thick oil foaming agent and preparation method and application thereof |
| CN112956478A (en) * | 2021-02-19 | 2021-06-15 | 广西汇丰生物科技有限公司 | Synergistic composition and application thereof in pesticide preparation of aqueous suspension |
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Application publication date: 20100224 |