CN113372570A - Lignin glyceryl ether phosphate and preparation method and application thereof - Google Patents
Lignin glyceryl ether phosphate and preparation method and application thereof Download PDFInfo
- Publication number
- CN113372570A CN113372570A CN202110530421.5A CN202110530421A CN113372570A CN 113372570 A CN113372570 A CN 113372570A CN 202110530421 A CN202110530421 A CN 202110530421A CN 113372570 A CN113372570 A CN 113372570A
- Authority
- CN
- China
- Prior art keywords
- lignin
- ether phosphate
- cutting fluid
- glyceryl ether
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920005610 lignin Polymers 0.000 title claims abstract description 165
- ONVCYWPWSUZUAP-UHFFFAOYSA-N 3-(2,3-dihydroxypropoxy)propane-1,2-diol;phosphoric acid Chemical compound OP(O)(O)=O.OCC(O)COCC(O)CO ONVCYWPWSUZUAP-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title abstract description 35
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 40
- 239000010452 phosphate Substances 0.000 claims abstract description 40
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 37
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 22
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002173 cutting fluid Substances 0.000 claims description 58
- 230000007062 hydrolysis Effects 0.000 claims description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims description 24
- 230000004913 activation Effects 0.000 claims description 23
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 17
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 230000003213 activating effect Effects 0.000 claims description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 230000026731 phosphorylation Effects 0.000 claims description 9
- 238000006366 phosphorylation reaction Methods 0.000 claims description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000005520 cutting process Methods 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- 230000000865 phosphorylative effect Effects 0.000 claims description 4
- 239000000022 bacteriostatic agent Substances 0.000 claims description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000013556 antirust agent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 2
- 239000011232 storage material Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 238000003801 milling Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 29
- 229920000056 polyoxyethylene ether Polymers 0.000 abstract description 9
- 229940051841 polyoxyethylene ether Drugs 0.000 abstract description 9
- 239000008233 hard water Substances 0.000 abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- 229920000223 polyglycerol Polymers 0.000 abstract description 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 abstract description 2
- -1 alcohol ether carboxylate Chemical class 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000011259 mixed solution Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 229920001451 polypropylene glycol Polymers 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 7
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 7
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 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 4
- 238000001816 cooling Methods 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000003345 natural gas Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000003209 petroleum derivative Substances 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 235000010344 sodium nitrate Nutrition 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 229920000289 Polyquaternium Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/126—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
- C10M2215/222—Triazines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
Abstract
The invention relates to lignin glyceryl ether phosphate and a preparation method and application thereof, belonging to the technical field of chemical synthesis. The invention provides a method for preparing lignin glycerol ether phosphate and lignin glycerol ether phosphate prepared by the method, the preparation method does not add ethoxy long chain, lignin polyglycerol ether is prepared by reacting lignin with glycidol, and then lignin glycerol ether phosphate is prepared by phosphorization, and the preparation process is green and environment-friendly; the glycidol used in the preparation method contains hydroxyl, the hydroxyl content of the product can be improved compared with polyoxyethylene ether/polyoxypropylene ether, and the phosphorus content of the product is further improved through phosphorization in the preparation method, so that the water solubility of the product is effectively improved, and therefore, the lignin glyceryl ether phosphate prepared by the method can be well dissolved in low-temperature hard water and is convenient to use in cold regions.
Description
Technical Field
The invention relates to lignin glyceryl ether phosphate and a preparation method and application thereof, belonging to the technical field of chemical synthesis.
Background
Modern industry is rapidly developing, and in order to manufacture various metal products, it is necessary to add cutting fluid in the process of metal cutting and grinding. The cutting fluid is compounded by various functional additives such as petroleum, surfactant and the like, and has good cooling, lubricating, corrosion inhibiting and other properties. However, these functional aids often contain elements that are harmful to the environment and the human body. Meanwhile, the petroleum in the cutting fluid belongs to non-renewable resources, and along with continuous drawing of human beings, the petroleum resources are increasingly exhausted.
Lignin has received increasing attention as a natural polymer compound rich in nature. At present, there is a method for obtaining a surfactant for use in a cutting fluid by adding polyethylene oxide or sulfonation to increase flexibility and hydrophilicity of lignin. However, the existing methods for preparing the surfactant for the cutting fluid by using lignin as a raw material have significant defects, such as:
patent document CN107973908B discloses an end-group sulfonate lignin polyether, which is prepared by preparing a chloro-alkenyl polyethylene glycol intermediate, then dropwise adding the chloro-alkenyl polyethylene glycol intermediate into lignin for reaction, and then adding a sulfonating agent, however, chlorine atoms are introduced in the reaction of the method, and a large amount of chlorine-containing wastewater is easily generated;
patent document CN105664787B discloses an amphoteric lignin-based surfactant, which is prepared by reacting lignin and lauryl alcohol glycidyl ether at 60-80 ℃; patent document CN109433099A discloses a sodium lignin-based alcohol ether carboxylate prepared by reacting lignin with octyl glycidyl ether at 60 to 80 ℃; the preparation method of the surfactant enhances the water solubility of lignin and reduces the surface tension of the lignin by introducing glycidyl ether, but the glycidyl ether introduced by the preparation method of the surfactant contains long carbon chains, so that the effect of improving the water solubility of the lignin is limited, and the use of the surfactant is limited.
Disclosure of Invention
To solve the above-mentioned drawbacks, the present invention provides a method for preparing a lignin glyceryl ether phosphate, wherein the method comprises the steps of:
the synthesis steps are as follows: reacting lignin with glycidol to obtain lignin glycerol ether;
and (3) phosphorization: and (3) phosphorizing the lignin glycerol ether by using a phosphorylation reagent to obtain the lignin glycerol ether phosphate. The molecular weight of the synthesized lignin glyceryl ether phosphate is 2500-7500 g/mol.
In one embodiment of the present invention, the synthesis step further comprises an activation step; the activation step is as follows: adding an activating agent into the alkaline lignin solution to obtain an activating system; and heating the activation system, and then performing reduced pressure dehydration to obtain activated lignin.
In one embodiment of the present invention, the activating step is: dissolving lignin in an alkaline solution, and adjusting the pH value to 9-13 to obtain an alkaline lignin solution; adding an activating agent into the alkaline lignin solution to obtain an activating system; and (3) heating the activation system under the condition of 300-600 rpm while stirring until the temperature of the activation system is raised to 50-70 ℃, and after the temperature is raised, performing reduced pressure dehydration on the activation system until the vacuum degree reaches-0.08 to-0.1 MPa to obtain activated lignin.
In one embodiment of the present invention, the synthesis step is: heating the activated lignin to 90-120 ℃, and then dropwise adding glycidol into the activated lignin to obtain a synthesis system; and (3) reacting the synthesis system at 100-150 ℃ until the pressure is constant to obtain the lignin glyceryl ether.
In one embodiment of the invention, the duration of the dropwise addition is 2-8 h.
In one embodiment of the invention, the molecular weight of the lignin is 2000-5000 g/mol.
In one embodiment of the invention, the molar ratio of lignin to glycidol is 1: 1 to 8.
In one embodiment of the present invention, the phosphating step is: adding a phosphorylation reagent into lignin glycerol ether to obtain a phosphorylation system; and reacting the phosphating system at 50-80 ℃ for 2-3 h to obtain a reaction product.
In one embodiment of the present invention, the phosphating step is: after the temperature of the lignin glyceryl ether is reduced to 25-30 ℃, adding a phosphorylation reagent in batches while stirring at the rotation speed of 800-1000 rpm at the temperature of 25-30 ℃ to obtain a phosphating system; and heating the phosphating system to 50-80 ℃, and reacting for 2-3 h at 50-80 ℃ to obtain a reaction product.
In one embodiment of the present invention, the phosphating step is followed by a hydrolysis step; the hydrolysis step comprises the following steps: adding a hydrolytic agent into a product obtained in the phosphorization step to obtain a hydrolysis system; and hydrolyzing the hydrolysis system at 70-100 ℃ for 0.5-2 h to obtain the lignin glyceryl ether phosphate.
In one embodiment of the present invention, the hydrolysis step is: heating the product obtained in the phosphorization step and dripping a hydrolysis agent until the temperature of the product obtained in the phosphorization step is raised to 70-100 ℃ to obtain a hydrolysis system; and hydrolyzing the hydrolysis system at 70-100 ℃ for 0.5-2 h to obtain the lignin glyceryl ether phosphate.
In one embodiment of the present invention, the mass ratio of the lignin, the activator, the glycidol, the hydrolyzing agent and the phosphorylating agent is 100: 3-7: 1.5-30: 0.5-2: 3.5 to 16.
In one embodiment of the present invention, the batch addition of the phosphorylating agent is: adding the phosphorylation reagents into the lignin glyceryl ether in 4-7 batches, wherein the adding time interval of each batch of the phosphorylation reagents is 10-15 min.
In one embodiment of the invention, the phosphating step and the hydrolysis step are both carried out under nitrogen protection.
In one embodiment of the invention, the phosphorylating agent is at least one of phosphoric acid, pyrophosphoric acid, phosphorus oxychloride and phosphorus pentoxide.
In one embodiment of the present invention, the alkaline solution is at least one of a 10 wt% aqueous sodium hydroxide solution and a 10 wt% aqueous potassium hydroxide solution.
In one embodiment of the present invention, the activating agent is at least one of hydrogen peroxide, oxygen, ozone and potassium permanganate.
In one embodiment of the invention, the activating agent is hydrogen peroxide with a concentration of 20-30 wt%.
In one embodiment of the present invention, the hydrolysis agent is at least one of hydrogen peroxide and deionized water.
In one embodiment of the invention, the hydrolytic agent is hydrogen peroxide or deionized water with a concentration of 20-30 wt%.
The invention also provides lignin glycerol ether phosphate which is prepared by using the method.
The invention also provides a cutting fluid, which contains the lignin glyceryl ether phosphate.
In one embodiment of the present invention, the cutting fluid contains the above-mentioned lignin glyceryl ether phosphate and a nonionic surfactant.
In one embodiment of the present invention, the cutting fluid contains: the cutting fluid comprises an alkali storage agent accounting for 2-20% of the total mass of the cutting fluid, a bacteriostatic agent accounting for 0.5-2% of the total mass of the cutting fluid, lignin glyceryl ether phosphate accounting for 20-40% of the total mass of the cutting fluid, a nonionic surfactant accounting for 5-20% of the total mass of the cutting fluid, an antirust agent accounting for 0.5-4% of the total mass of the cutting fluid and the balance of water.
In one embodiment of the invention, the base stock agent is at least one of optimized triethanolamine, optimized diethanolamine, optimized triisopropanolamine, and N-methyldiethanolamine.
In one embodiment of the present invention, the bacteriostatic agent is at least one of borate, triazine derivative, morpholine derivative, polyquaternium and isothiazolinone.
In one embodiment of the invention, the nonionic surfactant is at least one of optimized 1720 and optimized 1740.
In one embodiment of the present invention, the rust inhibitor is at least one of suberic acid, azelaic acid, sebacic acid, neodecanoic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, and tetradecanedioic acid.
The invention also provides application of the lignin glyceryl ether phosphate as a surfactant.
The invention also provides application of the lignin glyceryl ether phosphate or the cutting fluid in daily use chemicals, textiles, metal cutting or metal grinding.
The technical scheme of the invention has the following advantages:
1. the invention provides a method for preparing lignin glycerol ether phosphate and lignin glycerol ether phosphate prepared by the method, wherein ethoxy long chains are not added in the preparation method, lignin polyglycerol ether is prepared by reacting lignin with glycidol, and then lignin glycerol ether phosphate is prepared by phosphorization; the preparation method has the following advantages:
(1) the glycidol used in the preparation method contains hydroxyl, so that the hydroxyl content of the product can be improved compared with polyoxyethylene ether/polyoxypropylene ether, and the phosphorus content of the product is further improved through phosphorization in the preparation method, so that the water solubility of the product is effectively improved, and therefore, the lignin glyceryl ether phosphate prepared by the method can be well dissolved in low-temperature hard water and is convenient to use;
(2) when the lignin glyceryl ether phosphate prepared by the preparation method is applied to the cutting fluid, the phosphate and a rigid macromolecular structure in the lignin can generate a synergistic effect, so that the extreme pressure wear resistance of the cutting fluid is improved to a great extent, and extra extreme pressure agents and corrosion inhibitors can be reduced or even not added into the cutting fluid;
(3) the lignin glyceryl ether phosphate prepared by the preparation method has excellent lubricity and corrosion inhibition, so that the lignin glyceryl ether phosphate prepared by the preparation method can be used as an excellent surfactant and is widely applied to the fields of daily chemical cleaning, spinning, metal cutting or metal grinding and the like;
(4) the lignin glyceryl ether phosphate prepared by the preparation method has the characteristics of good thermal stability, good low-temperature fluidity and capability of being used in low-temperature areas, can replace toxic chemicals such as nonyl phenol polyether phosphate and the like in the field of metal processing, and has the advantages of environmental protection and no toxicity when being applied to metal cutting fluid;
(5) the lignin glyceryl ether phosphate prepared by the preparation method has the characteristic of low foaming, and the problem of possible failure of a follow-up defoaming agent caused by the addition of the defoaming agent in the existing metal cutting fluid can be effectively solved by applying the lignin glyceryl ether phosphate to the metal cutting fluid;
(6) the preparation method for preparing the lignin glyceryl ether phosphate does not need to use a solvent or prepare a chlorinated intermediate, does not need to introduce chlorine atoms in the reaction, and has the advantages of environmental protection, simple steps and difficulty in generating a large amount of chlorine-containing wastewater.
Furthermore, the existing preparation method of the lignin-based surfactant usually needs to react lignin and glycidyl ether in a sodium hydroxide aqueous solution at a lower temperature, so that the activity is lower, and the ring-opening reaction is difficult to realize.
Furthermore, the preparation method converts the polyphosphate ester generated in the reaction into the monoester and the diester through a hydrolysis step, thereby effectively avoiding the influence of the generated by-products on the water solubility of the product.
2. The invention provides a cutting fluid containing the lignin glyceryl ether phosphate; the cutting fluid has the advantages of easy cleaning, low foam, extreme pressure abrasion resistance, corrosion inhibition, green and low toxicity, capability of reducing the addition of an auxiliary agent, capability of avoiding excessive waste of resources, environmental protection and the like.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The following examples do not show specific experimental procedures or conditions, and can be performed according to the procedures or conditions of the conventional experimental procedures described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
Example 1: lignin glyceryl ether phosphate and preparation method thereof
The embodiment provides lignin glycerol ether phosphate, and the preparation method of the lignin glycerol ether phosphate comprises the following steps:
an activation step: dissolving 100kg of lignin (the number average molecular weight is 2000g/mol) in a 10 wt% sodium hydroxide aqueous solution to obtain a mixed solution (the mass fraction of the lignin in the mixed solution is 40%); after the pH value of the mixed solution is adjusted to 9, pouring the mixed solution into a reaction kettle; 7kg of hydrogen peroxide with the concentration of 30 wt% is dropwise added into the reaction kettle to obtain an activation system; stirring and heating the activation system at 300rpm until the temperature of the activation system is raised to 50 ℃, and after the temperature is raised, performing reduced pressure dehydration on the activation system until the vacuum degree reaches-0.1 MPa to obtain activated lignin;
the synthesis steps are as follows: heating the activated lignin to 90 ℃, dropwise adding 1.5kg of glycidol into the activated lignin, and dropwise adding for 1h to obtain a synthesis system; reacting the synthesis system at 100 ℃ until the pressure is constant to obtain lignin glyceryl ether;
and (3) phosphorization: introducing nitrogen into the reaction kettle, cooling the lignin glyceryl ether to 25 ℃, adding 15kg of phosphorus oxychloride into the lignin glyceryl ether in batches while stirring at the rotation speed of 800rpm at the temperature of 25 ℃, and adding 3kg of phosphorus oxychloride every 15min to obtain a phosphating system; heating, namely heating the phosphating system to 50 ℃, and reacting for 3 hours at 50 ℃ to obtain a reaction product;
a hydrolysis step: heating the reaction product and dripping 1kg of deionized water until the temperature of the reaction product is raised to 70 ℃ to obtain a hydrolysis system; hydrolyzing the hydrolysis system at 70 ℃ for 2h to obtain the lignin glyceryl ether phosphate.
The lignin glyceryl ether phosphate ester has the number average molecular weight of 2519.2g/mol according to GPC test, and has the monoester content of 52.6% and the diester content of 46.5% according to titration test;
wherein, GPC measurement adopts Shimadzu gel permeation chromatography system to carry out determination: polyethylene glycol is used as a standard substance, the mobile phase is 0.1mol/L sodium nitrate, the column temperature is 40 ℃, the flow rate is 0.8mL/min, the sample injection amount is 100 mu L, and the sample concentration is 2 g/L;
the titration method is described in the literature "synthesis and application of phosphoric acid ester surfactants in Tang Yongfan [ J ]. Petroleum and Natural gas chemical industry, 1995,24(1):28-33 ].
Example 2: lignin glyceryl ether phosphate and preparation method thereof
The embodiment provides lignin glycerol ether phosphate, and the preparation method of the lignin glycerol ether phosphate comprises the following steps:
an activation step: dissolving 100kg of lignin (the number average molecular weight is 3000g/mol) in a sodium hydroxide solution with the concentration of 10 wt% to obtain a mixed solution (the mass fraction of the lignin in the mixed solution is 40%); after the pH value of the mixed solution is adjusted to 11.5, pouring the mixed solution into a reaction kettle; dropwise adding 5kg of hydrogen peroxide with the concentration of 30 wt% into a reaction kettle to obtain an activation system; heating the activation system under the condition of 400rpm while stirring until the temperature of the activation system is raised to 60 ℃, and after the temperature is raised, performing reduced pressure dehydration on the activation system until the vacuum degree reaches-0.09 MPa to obtain activated lignin;
the synthesis steps are as follows: heating the activated lignin to 115 ℃, dropwise adding 15kg of glycidol into the activated lignin, and dropwise adding for 4 hours to obtain a synthesis system; reacting the synthesis system at 115 ℃ until the pressure is constant to obtain lignin glyceryl ether;
and (3) phosphorization: introducing nitrogen into the reaction kettle, cooling the lignin glyceryl ether to 25 ℃, adding 8kg of phosphorus pentoxide into the lignin glyceryl ether in batches at the temperature of 25 ℃ and the rotating speed of 1000rpm while stirring, and adding 2kg of phosphorus pentoxide every 15min to obtain a phosphating system; heating, namely heating the phosphating system to 70 ℃, and reacting for 3 hours at 70 ℃ to obtain a reaction product;
a hydrolysis step: heating the reaction product and dropwise adding 2kg of hydrogen peroxide with the concentration of 20 wt% until the temperature of the reaction product is raised to 80 ℃ to obtain a hydrolysis system; hydrolyzing the hydrolysis system at 80 ℃ for 1h to obtain the lignin glyceryl ether phosphate.
The lignin glyceryl ether phosphate ester has the number average molecular weight of 3351.9g/mol according to GPC test, and the monoester content of 54.6% and the diester content of 40.5% according to titration test;
wherein, GPC measurement adopts Shimadzu gel permeation chromatography system to carry out determination: polyethylene glycol is used as a standard substance, the mobile phase is 0.1mol/L sodium nitrate, the column temperature is 40 ℃, the flow rate is 0.8mL/min, the sample injection amount is 100 mu L, and the sample concentration is 2 g/L;
the titration method is described in the literature "synthesis and application of phosphoric acid ester surfactants in Tang Yongfan [ J ]. Petroleum and Natural gas chemical industry, 1995,24(1):28-33 ].
Example 3: lignin glyceryl ether phosphate and preparation method thereof
The embodiment provides lignin glycerol ether phosphate, and the preparation method of the lignin glycerol ether phosphate comprises the following steps:
an activation step: dissolving 100kg of lignin (with the number average molecular weight of 5000g/mol) in a sodium hydroxide solution with the concentration of 10 wt% to obtain a mixed solution (the mass fraction of the lignin in the mixed solution is 40%); after the pH value of the mixed solution is adjusted to 13, pouring the mixed solution into a reaction kettle; dropwise adding 3kg of hydrogen peroxide with the concentration of 30 wt% into a reaction kettle to obtain an activation system; heating the activation system under stirring at 600rpm until the temperature of the activation system is raised to 70 ℃, and after the temperature is raised, performing reduced pressure dehydration on the activation system until the vacuum degree reaches-0.08 MPa to obtain activated lignin;
the synthesis steps are as follows: heating the activated lignin to 150 ℃, dropwise adding 30kg of glycidol into the activated lignin for 8 hours to obtain a synthesis system; reacting the synthesis system at 150 ℃ until the pressure is constant to obtain lignin glyceryl ether;
and (3) phosphorization: introducing nitrogen into the reaction kettle, cooling the lignin glyceryl ether to 30 ℃, adding 3.5kg of phosphorus pentoxide into the lignin glyceryl ether in batches at the temperature of 30 ℃ and the rotating speed of 900rpm while stirring, and adding 0.5kg of phosphorus pentoxide every 10min to obtain a phosphating system; heating, namely heating the phosphating system to 80 ℃, and reacting for 2 hours at 80 ℃ to obtain a reaction product;
a hydrolysis step: heating the reaction product and dropwise adding 0.5kg of 30 wt% hydrogen peroxide until the temperature of the reaction product is raised to 100 ℃ to obtain a hydrolysis system; hydrolyzing the hydrolysis system at 100 ℃ for 2h to obtain the lignin glyceryl ether phosphate.
The lignin glyceryl ether phosphate ester has the number average molecular weight of 7420.4g/mol according to GPC test, and the monoester content of 40.1% and the diester content of 49.2% according to titration test;
wherein, GPC measurement adopts Shimadzu gel permeation chromatography system to carry out determination: polyethylene glycol is used as a standard substance, the mobile phase is 0.1mol/L sodium nitrate, the column temperature is 40 ℃, the flow rate is 0.8mL/min, the sample injection amount is 100 mu L, and the sample concentration is 2 g/L;
the titration method is described in the literature "synthesis and application of phosphoric acid ester surfactants in Tang Yongfan [ J ]. Petroleum and Natural gas chemical industry, 1995,24(1):28-33 ].
Comparative example 1: lignin polyoxyethylene ether phosphate and preparation method thereof
The comparative example provides lignin polyoxyethylene ether phosphate, and the preparation method of the lignin polyoxyethylene ether phosphate comprises the following steps: based on example 1, glycidol was replaced with ethylene oxide to give a lignin polyoxyethylene ether phosphate.
Comparative example 2: lignin polyoxypropylene ether phosphate and preparation method thereof
The comparative example provides a lignin polyoxypropylene ether phosphate, which is prepared by the following steps: in addition to example 1, glycidol was replaced with propylene oxide to give lignin polyoxypropylene ether phosphate.
Experimental example 1: water solubility test of Lignin Glycerol Ether phosphate
The water solubility of the lignin glyceryl ether phosphate obtained in examples 1 to 3 in hard water at 25 ℃ was examined using the amphoteric lignin-based surfactant obtained by the method described in example 1 of patent document CN105664787B, the sodium lignin-based alcohol ether carboxylate obtained by the method described in example 1 of patent document CN109433099A, and the lignin polyoxypropylene ether phosphate obtained in comparative example 2 as control 1, control 2, and control 3, respectively;
the detection method comprises the following steps: adding the amphoteric lignin-based surfactant of the control group 1, the sodium lignin-based alcohol ether carboxylate of the control group 2, the lignin polyoxypropylene ether phosphate of the control group 3 and the lignin glyceryl ether phosphate prepared in the examples 1-3 into hard water at the temperature of 25 ℃, stirring for 15s, and preparing into an aqueous solution with the concentration of 10 wt%;
wherein, hard water is tap water taken from a faucet, and the hardness of the hard water is measured to be 20 degrees by a water hardness online water quality analyzer;
the detection result is as follows: an aqueous solution prepared from the lignin glyceryl ether phosphate prepared in the embodiment 1-3 is clear and transparent, and is easily dissolved in low-temperature hard water; the aqueous solution prepared by using the amphoteric lignin-based surfactant of the control group 1, the sodium lignin-based alcohol ether carboxylate of the control group 2 and the lignin polyoxypropylene ether phosphate of the control group 3 was turbid and was not easily dissolved in low-temperature hard water.
Experimental example 2: foam performance test of lignin glyceryl ether phosphate
The foaming performance of the lignin glyceryl ether phosphate prepared in examples 1-3 was tested by using the lignin polyoxyethylene ether phosphate prepared in comparative example 1 and the lignin polyoxypropylene ether phosphate prepared in comparative example 2 as a control group 1 and a control group 2, respectively;
the detection method comprises the following steps: after the lignin polyoxyethylene ether phosphate prepared in comparative example 1, the lignin polyoxypropylene ether phosphate prepared in comparative example 2 and the lignin glyceryl ether phosphate prepared in examples 1-3 were respectively prepared into 0.2 wt% aqueous solutions with distilled water, the foam properties were measured by the foam height of each time period using a Ross-Milles bubble height, and the test results are shown in table 1.
As can be seen from Table 1, the lignin glyceryl ether phosphate esters obtained in examples 1 to 3 had less foam and broke down more quickly than the lignin polyoxyethylene ether phosphate ester obtained in comparative example 1 and the lignin polyoxypropylene ether phosphate ester obtained in comparative example 2.
TABLE 1 foam Properties of different cutting fluids
Example 4: cutting fluid
The embodiment provides a cutting fluid, which comprises the following components:
10kg of triethanolamine, 5kg of N-methyldiethanolamine, 0.5kg of isothiazolinone, 20kg of lignin glyceryl ether phosphate in example 1, 172020 kg of lignin, 0.5kg of suberic acid and 44kg of water.
The preparation method of the cutting fluid comprises the following steps:
weighing water, optimized 1740 and the lignin glyceryl ether phosphate, the optimized triisoethanolamine, N-methyldiethanolamine, suberic acid and isothiazolinone in the embodiment 1 according to the mass ratio, and uniformly mixing to obtain the cutting fluid.
Example 5: cutting fluid
The embodiment provides a cutting fluid, which comprises the following components:
7kg of optimized triethanolamine, 3kg of N-methyldiethanolamine, 0.5kg of isothiazolinone, 35kg of lignin glyceryl ether phosphate in example 2, 17405 kg of optimized lignin glyceryl ether phosphate, 4kg of neodecanoic acid and 47.5kg of water.
The preparation method of the cutting fluid comprises the following steps:
weighing water, optimized 1740 and the lignin glyceryl ether phosphate, the optimized triethanolamine, N-methyldiethanolamine, neodecanoic acid and isothiazolinone in the embodiment 2 according to the mass, and uniformly mixing to obtain the cutting fluid.
Example 6: cutting fluid
The embodiment provides a cutting fluid, which comprises the following components:
10kg of optimized diethanolamine, 0.5kg of triazine derivative, 25kg of lignin glycerol ether phosphate in example 3, 174015 kg of optimized, 4kg of neodecanoic acid and 47.5kg of water.
The preparation method of the cutting fluid comprises the following steps:
weighing water, optimized 1740 and the lignin glyceryl ether phosphate, optimized diethanolamine, neodecanoic acid and triazine derivatives in example 3 according to the above quality, and mixing uniformly to obtain the cutting fluid.
Comparative example 3: cutting fluid
The present comparative example provides a cutting fluid having the following composition:
optimized triethanolamine 7kg, N-methyldiethanolamine 3kg, isothiazolinone 0.5kg, commercial phosphate 35kg, optimized 17405 kg, neodecanoic acid 4kg and water 47.5 kg.
The preparation method of the cutting fluid comprises the following steps:
weighing water, optimized 1740, commercially available phosphate ester (from macroze chemical industry), optimized triethanolamine, N-methyldiethanolamine, neodecanoic acid and isothiazolinone according to the above mass, and mixing uniformly to obtain the cutting fluid.
Experimental example 3: performance test of cutting fluid
The commercial THIF-111 cutting fluid (purchased from Hengxin chemical industry) and the comparative example 3 are used as a reference, main technical index tests are carried out on the cutting fluids in the examples 4-6 according to GB/T6144, and the test results are shown in Table 2.
As can be seen from Table 2, the cutting fluids of examples 4-6 all meet the national and industrial standards in terms of appearance, storage stability, defoaming property, surface tension, anti-rust property, corrosion property and other performance and technical indexes. The cutting fluids of examples 4 to 6 are superior to those of the commercially available example and comparative example 3 in defoaming property, surface tension, rust prevention property, and the like, and the cutting fluid of example 5 is superior to those of examples 4 and 6 in performance in all respects.
TABLE 2 Properties of different cutting fluids
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. A process for preparing a lignin glyceryl ether phosphate, said process comprising the steps of:
the synthesis steps are as follows: reacting lignin with glycidol to obtain lignin glycerol ether;
and (3) phosphorization: and (3) phosphorizing the lignin glycerol ether by using a phosphorylation reagent to obtain the lignin glycerol ether phosphate.
2. The method of claim 1, wherein prior to the step of synthesizing, further comprising a step of activating; the activation step is as follows: adding an activating agent into the alkaline lignin solution to obtain an activating system; heating the activation system, and then performing reduced pressure dehydration to obtain activated lignin;
preferably, the activating agent is at least one of hydrogen peroxide, oxygen, ozone and potassium permanganate.
3. The method of claim 2, wherein the synthesizing step is: heating the activated lignin to 90-120 ℃, and then dropwise adding glycidol into the activated lignin to obtain a synthesis system; reacting the synthesis system at 100-150 ℃ until the pressure is constant to obtain lignin glyceryl ether;
preferably, the molecular weight of the lignin is 2000-5000 g/mol, and the molar ratio of the lignin to glycidol is 1: 1 to 8.
4. The process according to any one of claims 1 to 3, wherein the phosphating step is: adding a phosphorylation reagent into lignin glycerol ether to obtain a phosphorylation system; reacting the phosphating system at 50-80 ℃ for 2-3 h to obtain a reaction product;
preferably, the phosphorylating agent is at least one of phosphoric acid, pyrophosphoric acid, phosphorus oxychloride and phosphorus pentoxide.
5. The process according to any one of claims 1 to 4, further comprising a hydrolysis step after the phosphating step; the hydrolysis step comprises the following steps: adding a hydrolytic agent into a product obtained in the phosphorization step to obtain a hydrolysis system; hydrolyzing the hydrolysis system at 70-100 ℃ for 0.5-2 h to obtain lignin glyceryl ether phosphate;
preferably, the hydrolytic agent is at least one of hydrogen peroxide and deionized water.
6. A lignin glycerol ether phosphate produced by the method according to any one of claims 1 to 5.
7. A cutting fluid comprising the lignin glyceryl ether phosphate according to claim 6.
8. The cutting fluid according to claim 7, wherein the cutting fluid comprises the lignin glyceryl ether phosphate according to claim 6 and a nonionic surfactant;
preferably, the cutting fluid comprises: the cutting fluid comprises an alkali storage agent accounting for 2-20% of the total mass of the cutting fluid, a bacteriostatic agent accounting for 0.5-2% of the total mass of the cutting fluid, lignin glyceryl ether phosphate accounting for 20-40% of the total mass of the cutting fluid, a nonionic surfactant accounting for 5-20% of the total mass of the cutting fluid, an antirust agent accounting for 0.5-4% of the total mass of the cutting fluid and the balance of water.
9. Use of the lignin glycerol ether phosphate of claim 6 as a surfactant.
10. Use of the lignin glycerol ether phosphate according to claim 6 or the cutting fluid according to claim 7 or 8 in daily use chemicals, textiles, metal cutting or metal milling processes.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115286899A (en) * | 2022-08-08 | 2022-11-04 | 上海汉禾生物新材料科技有限公司 | Toughening-flame-retardant bisphenol epoxy resin composite material and application thereof |
| CN115386102A (en) * | 2022-08-19 | 2022-11-25 | 广州大学 | Phosphorized lignosulfonate nanoparticle and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512276A (en) * | 1992-08-29 | 1996-04-30 | Wella Aktiengesellschaft | Composition for fixing hair based on lignin or lignin derivatives as well as dihydroxypropyl lignin |
| CN101327416A (en) * | 2008-08-01 | 2008-12-24 | 中国林业科学研究院林产化学工业研究所 | Lignose alcohol ether carboxylate surfactant and preparation method thereof |
| CN105461916A (en) * | 2015-10-29 | 2016-04-06 | 清华大学 | Preparation method of lignin-based polyether sulfonate surfactant |
| CN105664787A (en) * | 2016-02-16 | 2016-06-15 | 广州市日用化学工业研究所有限公司 | Amphoteric lignin-based surfactant and preparation method and application thereof |
| CN109433099A (en) * | 2018-12-26 | 2019-03-08 | 广东省稀有金属研究所 | A kind of preparation method and applications of lignin-base sodium alcohol ether carboxylate |
-
2021
- 2021-05-14 CN CN202110530421.5A patent/CN113372570B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512276A (en) * | 1992-08-29 | 1996-04-30 | Wella Aktiengesellschaft | Composition for fixing hair based on lignin or lignin derivatives as well as dihydroxypropyl lignin |
| CN101327416A (en) * | 2008-08-01 | 2008-12-24 | 中国林业科学研究院林产化学工业研究所 | Lignose alcohol ether carboxylate surfactant and preparation method thereof |
| CN105461916A (en) * | 2015-10-29 | 2016-04-06 | 清华大学 | Preparation method of lignin-based polyether sulfonate surfactant |
| CN105664787A (en) * | 2016-02-16 | 2016-06-15 | 广州市日用化学工业研究所有限公司 | Amphoteric lignin-based surfactant and preparation method and application thereof |
| CN109433099A (en) * | 2018-12-26 | 2019-03-08 | 广东省稀有金属研究所 | A kind of preparation method and applications of lignin-base sodium alcohol ether carboxylate |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115286899A (en) * | 2022-08-08 | 2022-11-04 | 上海汉禾生物新材料科技有限公司 | Toughening-flame-retardant bisphenol epoxy resin composite material and application thereof |
| CN115286899B (en) * | 2022-08-08 | 2023-06-16 | 上海汉禾生物新材料科技有限公司 | Toughening-flame-retardant bisphenol type epoxy resin composite material and application thereof |
| CN115386102A (en) * | 2022-08-19 | 2022-11-25 | 广州大学 | Phosphorized lignosulfonate nanoparticle and preparation method and application thereof |
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Denomination of invention: A Lignin Glycerol Ether Phosphate Ester and Its Preparation Method and Application Effective date of registration: 20231211 Granted publication date: 20220726 Pledgee: Industrial and Commercial Bank of China Maoming Branch Pledgor: JIAHUA CHEMICALS (MAOMING) Co.,Ltd. Registration number: Y2023980070590 |
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