CN103274973A - Alkyl dinaphthyl ether sulfonate and preparation method thereof - Google Patents
Alkyl dinaphthyl ether sulfonate and preparation method thereof Download PDFInfo
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- CN103274973A CN103274973A CN2013102317882A CN201310231788A CN103274973A CN 103274973 A CN103274973 A CN 103274973A CN 2013102317882 A CN2013102317882 A CN 2013102317882A CN 201310231788 A CN201310231788 A CN 201310231788A CN 103274973 A CN103274973 A CN 103274973A
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- alkyl
- dinaphthyl ether
- preparation
- dinaphthyl
- ether sulfonate
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- -1 Alkyl dinaphthyl ether Chemical compound 0.000 title claims abstract description 67
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 9
- 239000011230 binding agent Substances 0.000 claims abstract description 8
- 239000006227 byproduct Substances 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- ARNKHYQYAZLEEP-UHFFFAOYSA-N 1-naphthalen-1-yloxynaphthalene Chemical compound C1=CC=C2C(OC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ARNKHYQYAZLEEP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- ILQHFISNNSQESO-UHFFFAOYSA-N naphthalene;hydrobromide Chemical compound Br.C1=CC=CC2=CC=CC=C21 ILQHFISNNSQESO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000003068 static effect Effects 0.000 claims description 5
- 239000002351 wastewater Substances 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 3
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 239000004571 lime Substances 0.000 claims description 3
- DMDOTRUOIVBPSF-UHFFFAOYSA-N naphthalene;hydrochloride Chemical compound Cl.C1=CC=CC2=CC=CC=C21 DMDOTRUOIVBPSF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960004418 trolamine Drugs 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 235000015320 potassium carbonate Nutrition 0.000 claims 2
- 235000017550 sodium carbonate Nutrition 0.000 claims 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 1
- PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 claims 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 1
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- RQQDJYROSYLPPK-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 Chemical compound N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 RQQDJYROSYLPPK-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- VDTFISGKJZGCTH-UHFFFAOYSA-N naphthalene hydroiodide Chemical compound I.C1=CC=CC2=CC=CC=C21 VDTFISGKJZGCTH-UHFFFAOYSA-N 0.000 claims 1
- QEUWOEGDLXKUNJ-UHFFFAOYSA-N naphthalene;hydrofluoride Chemical compound F.C1=CC=CC2=CC=CC=C21 QEUWOEGDLXKUNJ-UHFFFAOYSA-N 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 230000019635 sulfation Effects 0.000 claims 1
- 238000005670 sulfation reaction Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract 2
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 239000003945 anionic surfactant Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- URVHSUKDZZAPTI-UHFFFAOYSA-N 2-dodecylnaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(CCCCCCCCCCCC)=CC=C21 URVHSUKDZZAPTI-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000004945 emulsification Methods 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- FHRPPAKHJATMEV-UHFFFAOYSA-N 2-octadecylnaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(CCCCCCCCCCCCCCCCCC)=CC=C21 FHRPPAKHJATMEV-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 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 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000035800 maturation Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 238000012356 Product development Methods 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- MORMPWNLQJTSOT-UHFFFAOYSA-L disodium;4-dodecyl-2-(4-sulfonatophenoxy)benzenesulfonate Chemical compound [Na+].[Na+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C(OC=2C=CC(=CC=2)S([O-])(=O)=O)=C1 MORMPWNLQJTSOT-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a novel anionic surfactant alkyl dinaphthyl ether sulfonate and a preparation method thereof. The method comprises the steps as follows: halonaphthalenes and alkyl naphthol are taken as main raw materials; with the presence of an acid-binding agent, a catalyst and water absorbent, the main raw materials are subjected to heat preservation for 1-5 hours at the temperature ranging from 80 DEG C to180 DEG C to generate an intermediate product of alkyl dinaphthyl ether and a byproduct of halogen salt; halogen salt and the catalyst are filtered and removed, and alkyl dinaphthyl ether is obtained by rectifying and separating; and a sulfonating agent is added to alkyl dinaphthyl ether step by step, sulfonation is performed at the temperature in a range from 0 to 80 DEG C to generate alkyl dinaphthyl ether sulfoacid, and an antalkali is added to generate alkyl dinaphthyl ether sulfonate.
Description
Technical field
The invention belongs to tensio-active agent manufacturing technology field, be specifically related to a kind of alkyl dinaphthyl ether sulfonate and preparation method thereof.
Background technology
This product alkyl dinaphthyl ether sulfonate mainly is divided into alkyl dinaphthyl ether monosulfonate, alkyl dinaphthyl ether disulfonate, alkyl dinaphthyl ether trisulfonate, two alkyl dinaphthyl ether disulfonate, products such as two alkyl dinaphthyl ether trisulfonates, and domestic still do not have an example.I to the conditions of demand of high stability, cost performance, the wetting excellent surfactant of emulsification, have developed these series product according to several years of product development and application experience and market.Product can have extensive use at industrial circles such as oil production, textile printing and dyeing, latex processing, metal processing, surface cleaning, and product adopts Williamson's synthesis method to do the etherification reaction of this product, technology theory maturation, easy handling.
Summary of the invention
Goal of the invention: in order to develop a kind of more stable excellent surfactant of performance under different acid, alkali, inorganic salt, the temperature working conditions that has, the invention provides the negatively charged ion novel surfactant of a kind of macromole, many hydrophilic groups;
The present invention specifically realizes with following steps:
(1) 1-10mol naphthalene halide and 1-3mol alkyl naphthol are dropped into etherifying reactor;
(2) drop into acid binding agent and water-retaining agent to etherifying reactor, nitrogen protection simultaneously, stirring reaction is molten entirely to acid binding agent;
(3) drop into catalyzer to etherifying reactor, under 80-180 ℃ of temperature condition, be incubated 1-5 hour, generate intermediates alkyl dinaphthyl ether and by-product halogen;
(4) above-mentioned (3) product is filtered filtering by-product halogen and catalyzer;
(5) above-mentioned (4) product is carried out rectifying, divide and remove naphthalene halide, get the alkyl dinaphthyl ether, send into the sulfonation still;
(6) add inert organic solvents and 1-5mol sulphonating agent 0-80 ℃ of sulfonation to the sulfonation still again, be incubated 1-5 hour, the mixture of generation alkyl dinaphthyl ether sulfonic acid and inert solvent;
(7) add the water of material total amount 10-60% in the still to the sulfonation still, stir the static acid out in back, treat to divide after the layering and go waste water layer, oil reservoir to be alkyl dinaphthyl ether sulfonic acid, during the gained material is sent into and still;
(8) in and still add water and add alkaline neutraliser 1-5mol and be neutralized to neutrality, namely get alkyl dinaphthyl ether sulfonate;
Effect of the present invention and benefit are:
(1) aspect synthetic technology: adopt Williamson's synthesis method etherificate route synthesis of alkyl phenyl ether, technology theory maturation, product yield height;
(2) aspect economic benefit: not only the disodium 4-dodecyl-2,4 '-oxydibenzenesulfonate of alternative import is used for emulsification, dispersed demanding field, reduced the interests loss of national industry, and because the buying of production domesticization back becomes convenient, improved production and operation efficient;
(3) aspect product performance: this excellent product performance, both had anti-strong acid, highly basic, properties such as inorganic salt, surface tension can reach the 29-35 dynes per centimeter when concentration 0.1%, and have remarkable emulsifying property, and cheap, and cost performance is good.Product also alternative commercially available alkylphenol polyoxyethylene, sodium alkyl benzene sulfonate, alkyl sodium sulfonate, fatty alcohol-polyoxyethylene ether in industrial circles such as oil production, textile printing and dyeing, latex processing, metal processing, surface cleaning.Aspect emulsification, dispersing property, acid-and base-resisting, inorganic salt, high-temperature behavior, be that present commercially available alkylphenol polyoxyethylene, sodium alkyl benzene sulfonate, fatty alcohol-polyoxyethylene ether etc. are wetting, the 2-10 of dispersion, emulsification class tensio-active agent doubly.When increasing substantially product stability in use and effect, reduce usage quantity significantly, reduced use cost, reduced the environmental pollution index because using tensio-active agent to cause simultaneously;
Embodiment
Below by embodiment, further illustrate the present invention, this embodiment only is the present invention is described and never limits the present invention:
Embodiment 1
In reactor, add about 650 grams of naphthalene bromide and about 296 grams of dodecyl naphthols, add about 30 grams of solid sodium hydroxide, add about 21 grams of solid potassium hydroxide, the solid alkali that is stirred to adding all dissolves, add dewatering agent anhydrous magnesium sulfate 15, about 15 grams of cuprous chloride, heat up, and unlatching nitrogen protection, under 80-160 ℃ of temperature condition, be incubated 1-5 hour, be entirely reaction end with the dodecyl naphthol reaction, after terminal point arrives, the secondary filter filtration catalizer, by-product Sodium Bromide and Potassium Bromide and water-retaining agent, rectifying separation is fallen the naphthalene bromide of 281-285 ℃ of cut, get the dodecyl dinaphthyl ether, add sherwood oil 200 grams to the dodecyl dinaphthyl ether, under agitation drip 105 oleums, 300 grams, temperature control finishes reaction 1-5 hour at 0-80 ℃, surveys terminal point, after terminal point arrives, add water 500 grams, stir the static acid out in back, divide and go waste water layer, the gained oil reservoir is the mixture of dodecyl dinaphthyl ether disulfonic acid and sherwood oil, sherwood oil is extracted in decompression, adds water and add liquid caustic soda to dodecyl dinaphthyl ether disulfonic acid then to be neutralized to pH value 6.5-7.5 with a small amount of lime, filters, the filtrate moisturizing is to finished product content about 45%, get about 1115 grams of dodecyl dinaphthyl ether sodium disulfonate finished product, in the dodecyl naphthols, yield reaches more than 99%;
Embodiment 2
In reactor, add about 800 grams of naphthalene chloride and about 381 grams of octadecyl naphthols, add about 30 grams of solid sodium hydroxide, add about 21 grams of solid potassium hydroxide, the solid alkali that is stirred to adding all dissolves, add dewatering agent anhydrous magnesium sulfate 15, about 15 grams of cuprous chloride, heat up, and unlatching nitrogen protection, under 80-160 ℃ of temperature condition, be incubated 1-5 hour, be entirely reaction end with the octadecyl naphthol reaction, after terminal point arrives, the secondary filter filtration catalizer, byproduct sodium chloride and Repone K and water-retaining agent, rectifying separation is fallen the naphthalene chloride of 259-263 ℃ of cut, get the octadecyl dinaphthyl ether, add sherwood oil 200 grams to the octadecyl dinaphthyl ether, under agitation drip 105 oleums, 300 grams, temperature control finishes reaction 1-5 hour at 0-80 ℃, surveys terminal point, after terminal point arrives, add water 500 grams, stir the static acid out in back, divide and go waste water layer, the gained oil reservoir is the mixture of octadecyl dinaphthyl ether disulfonic acid and sherwood oil, sherwood oil is extracted in decompression, adds water and add liquid caustic soda to octadecyl dinaphthyl ether disulfonic acid then to be neutralized to pH value 6.5-7.5 with a small amount of lime, filters, the filtrate moisturizing is to finished product content about 45%, get about 1300 grams of octadecyl dinaphthyl ether sodium disulfonate finished product, in the octadecyl naphthols, yield reaches more than 99%;
Embodiment 3
In reactor, add about 1000 grams of naphthalene bromide and about 465 grams of two dodecyl naphthols; add about 30 grams of solid sodium hydroxide; add about 21 grams of solid potassium hydroxide; the solid alkali that is stirred to adding all dissolves; add dewatering agent anhydrous magnesium sulfate 15; about 30 grams of cuprous chloride; heat up; and unlatching nitrogen protection; under 80-160 ℃ of temperature condition; be incubated 1-5 hour; be entirely reaction end with two dodecyl naphthol reactions; after terminal point arrives; the secondary filter filtration catalizer; by-product Sodium Bromide and Potassium Bromide and water-retaining agent; rectifying separation is fallen the naphthalene bromide of 281-285 ℃ of cut; get two dodecyl dinaphthyl ethers, add 1,2-ethylene dichloride, 300 grams to two dodecyl dinaphthyl ethers; under agitation drip chlorsulfonic acid 205 grams; temperature control is at 0-80 ℃, and the hydrogen chloride gas of extraction generation simultaneously, finishes reaction 1-5 hour; survey terminal point; after terminal point arrives, add water 600 grams, stir the static acid out in back; divide and go waste water layer; the gained oil reservoir is the mixture of two dodecyl dinaphthyl ether disulfonic acid and sherwood oil, and sherwood oil is extracted in decompression, adds water and add trolamine to alkyl dinaphthyl ether disulfonic acid then to be neutralized to pH value 6.5-7.5; filter; the filtrate moisturizing is about 45% to finished product content, gets two dodecyl dinaphthyl ether disulfonic acid triethanolamine salts, about 1699 grams of finished product; in two dodecyl naphthols, yield reaches more than 99%.
Claims (11)
1. alkyl dinaphthyl ether sulfonate and preparation method thereof is characterized in that comprising following synthesis step and processing condition:
(1) 1-10mol naphthalene halide and 1-3mol alkyl naphthol are dropped into etherifying reactor;
(2) drop into acid binding agent and water-retaining agent to etherifying reactor, nitrogen protection simultaneously, stirring reaction is molten entirely to acid binding agent;
(3) drop into catalyzer to etherifying reactor, under 80-180 ℃ of temperature condition, be incubated 1-5 hour, generate intermediates alkyl dinaphthyl ether and by-product halogen;
(4) above-mentioned (3) product is filtered filtering by-product halogen and catalyzer;
(5) above-mentioned (4) product is carried out rectifying, divide and remove naphthalene halide, get the alkyl dinaphthyl ether, send into the sulfonation still;
(6) add inert organic solvents and 1-5mol sulphonating agent 0-80 ℃ of sulfonation to the sulfonation still again, be incubated 1-5 hour, the mixture of generation alkyl dinaphthyl ether sulfonic acid and inert solvent;
(7) add the water of material total amount 10-60% in the still to the sulfonation still, stir the static acid out in back, treat to divide after the layering and go waste water layer, oil reservoir to be alkyl dinaphthyl ether sulfonic acid, during the gained material is sent into and still;
(8) in and still add water and add alkaline neutraliser 1-5mol and be neutralized to pH value 6.5-7.5, namely get alkyl dinaphthyl ether sulfonate.
2. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof is characterized in that main raw material is: naphthalene halide alkyl naphthol, acid binding agent, sulphonating agent, alkaline neutraliser, water-retaining agent.
3. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof is characterized in that: synthesis material naphthalene halide: alkyl naphthol: acid binding agent: sulphonating agent: the molar ratio of alkaline neutraliser is 1-10: 1-3: 1-3:1-5: 1-5.
4. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described alkyl naphthol is that to comprise alkyl C number be 3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18 alkyl naphthol, and the alkyl of alkyl naphthol can be two alkyl or monoalkyl, can be normal chain alkyl or isomery alkyl.
5. a kind of alkyl diphenyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described naphthalene halide comprises: naphthalene chloride, naphthalene bromide, naphthalene iodide, naphthalene fluoride.
6. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described acid binding agent can be sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonate.
7. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described sulphonating agent comprises sulfuric acid, chlorsulfonic acid, thionamic acid, sulphur trioxide.
8. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described alkaline neutraliser can be mineral alkali: sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonate, lime etc. and organic amine series organic bases: trolamine, diethanolamine, thanomin, ammoniacal liquor, Monomethylamine, dimethylamine, Trimethylamine 99 etc.
9. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: the catalyzer in the described alkyl dinaphthyl ether synthesis technique is: benzo pyridine quinoline or three (3,6-dioxo alkyl) catalyzer of amine and mantoquita series, the catalyzer of mantoquita series can be the hydrosulfate of copper, the muriate of copper, the oxide compound of copper, ingredient proportion is the 1-10% of naphthalene halide and alkyl naphthol total amount, described water-retaining agent is the sulfation salt anhydride of magnesium, and dosage is 1-10%.
10. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof is characterized in that: sulfonic number can be 1-3 in the finished product structure, and alkyl can be 1-2.
11. a kind of alkyl dinaphthyl ether sulfonate according to claim 1 and preparation method thereof, it is characterized in that: described inert organic solvents can be trichloromethane, methylene dichloride, 1,2-ethylene dichloride, 1,1,2,2 ,-tetrachloroethane, Nitromethane 99Min., trieline, tetracol phenixin, o-nitroethylbenzene, oil of mirbane, nitrotoluene, orthodichlorobenzene, sherwood oil.
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| CN111548781A (en) * | 2020-06-05 | 2020-08-18 | 赛科思能源技术(重庆)有限责任公司 | Hypotonic oil field water injection pressure-reducing injection-increasing agent |
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| US20040034131A1 (en) * | 2002-08-16 | 2004-02-19 | General Electric Company | Antistatic and antidust agents, compositions thereof, and methods of manufacture |
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| CN108166257A (en) * | 2016-12-07 | 2018-06-15 | 上海东大化学有限公司 | A kind of silkete penetrating agent and preparation method thereof |
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