CN101589052A - 制造烷基氨基亚烷基膦酸的方法 - Google Patents
制造烷基氨基亚烷基膦酸的方法 Download PDFInfo
- Publication number
- CN101589052A CN101589052A CNA2007800458130A CN200780045813A CN101589052A CN 101589052 A CN101589052 A CN 101589052A CN A2007800458130 A CNA2007800458130 A CN A2007800458130A CN 200780045813 A CN200780045813 A CN 200780045813A CN 101589052 A CN101589052 A CN 101589052A
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- China
- Prior art keywords
- linearity
- aromaticity
- branching
- ring
- hydrocarbon chain
- 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.)
- Pending
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- -1 alkylamino alkylene phosphonic acids Chemical class 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000002243 precursor Substances 0.000 claims description 9
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 3
- 239000002455 scale inhibitor Substances 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003337 fertilizer Substances 0.000 claims description 2
- 239000011785 micronutrient Substances 0.000 claims description 2
- 235000013369 micronutrients Nutrition 0.000 claims description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- 239000000243 solution Substances 0.000 description 48
- 238000003756 stirring Methods 0.000 description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 238000004679 31P NMR spectroscopy Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 150000003009 phosphonic acids Chemical class 0.000 description 5
- 238000002360 preparation method Methods 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CFNHVUGPXZUTRR-UHFFFAOYSA-N n'-propylethane-1,2-diamine Chemical compound CCCNCCN CFNHVUGPXZUTRR-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 238000009156 water cure Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JONTXEXBTWSUKE-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)ethanamine Chemical compound NCCSCCN JONTXEXBTWSUKE-UHFFFAOYSA-N 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 229940061584 phosphoramidic acid Drugs 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/12—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/10—Nature of the water, waste water, sewage or sludge to be treated from quarries or from mining activities
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
Abstract
Description
Claims (9)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06025514A EP1932848A1 (en) | 2006-12-11 | 2006-12-11 | Process for the manufacture of alkylamino alkylene phosphonic acids |
EP06025514.8 | 2006-12-11 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410663113.XA Division CN104530123A (zh) | 2006-12-11 | 2007-12-11 | 制造烷基氨基亚烷基膦酸的方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN101589052A true CN101589052A (zh) | 2009-11-25 |
Family
ID=38115869
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2007800458130A Pending CN101589052A (zh) | 2006-12-11 | 2007-12-11 | 制造烷基氨基亚烷基膦酸的方法 |
CN201410663113.XA Pending CN104530123A (zh) | 2006-12-11 | 2007-12-11 | 制造烷基氨基亚烷基膦酸的方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410663113.XA Pending CN104530123A (zh) | 2006-12-11 | 2007-12-11 | 制造烷基氨基亚烷基膦酸的方法 |
Country Status (11)
Country | Link |
---|---|
US (2) | US8802891B2 (zh) |
EP (2) | EP1932848A1 (zh) |
JP (2) | JP5635263B2 (zh) |
CN (2) | CN101589052A (zh) |
BR (1) | BRPI0720093A8 (zh) |
CA (1) | CA2671308A1 (zh) |
ES (1) | ES2480945T3 (zh) |
MX (1) | MX2009006160A (zh) |
PL (1) | PL2125842T3 (zh) |
RU (1) | RU2498989C2 (zh) |
WO (1) | WO2008071689A2 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107957436B (zh) * | 2017-10-11 | 2021-01-29 | 深圳供电局有限公司 | 一种评估油浸纸绝缘组件的不均匀受潮程度的方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3705005A (en) | 1971-06-21 | 1972-12-05 | Betz Laboratories | Aminoalkylene phosphonate derivatives as corrosion inhibitors in aqueous systems |
US3974090A (en) | 1975-03-20 | 1976-08-10 | Monsanto Company | Imino alkylimino phosphonates and method for preparing and using same |
US4234411A (en) * | 1979-03-15 | 1980-11-18 | Uop Inc. | Fluid catalytic cracking process |
US4234511A (en) | 1979-07-26 | 1980-11-18 | Buckman Laboratories, Inc. | Dialkylamino-N,N-bis(phosphonoalkylene)alkylamines and use in aqueous systems as precipitation and corrosion inhibitors |
US4243479A (en) * | 1979-08-15 | 1981-01-06 | National Starch And Chemical Corporation | Novel starch ether derivatives, a method for the preparation thereof and their use in paper |
US4260738A (en) * | 1980-01-10 | 1981-04-07 | National Starch And Chemical Corporation | Novel starch ether derivatives, a method for the preparation thereof |
US4260730A (en) | 1980-01-03 | 1981-04-07 | Desoto, Inc. | Preparation of bisphenol-formaldehyde ethers using nitric acid |
SU960184A1 (ru) * | 1980-06-26 | 1982-09-23 | Предприятие П/Я А-7346 | Способ получени амино-N-трисметиленфосфоновой кислоты |
US4477390A (en) | 1981-08-21 | 1984-10-16 | Monsanto Company | Aminomethylenephosphonic acid solutions |
US4330487A (en) * | 1980-10-29 | 1982-05-18 | Petrolite Corporation | N,N-Dimethylene phosponic acids of alkylene diamines |
DE3128755A1 (de) * | 1981-07-21 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | 3-alkoxipropylenimino-bis(methylenphosphonsaeuren) und deren salze, verfahren zu deren herstellung und deren verwendung |
US4707306A (en) * | 1986-12-11 | 1987-11-17 | National Starch And Chemical Corporation | Alpha-aminomethylene phosphonate betaines and polymers prepared therewith |
GB2306465A (en) * | 1995-10-20 | 1997-05-07 | Albright & Wilson Uk Ltd | Scale inhibition using alkanolamine methylene phosphonate |
IT1304868B1 (it) * | 1998-07-07 | 2001-04-05 | Golden Lady Spa | Metodo e dispositivo per la chiusura della punta di un manufattotubolare su una macchina da maglieria |
WO2000018695A2 (en) * | 1998-09-30 | 2000-04-06 | Albright & Wilson Uk Limited | Water treatment |
-
2006
- 2006-12-11 EP EP06025514A patent/EP1932848A1/en not_active Withdrawn
-
2007
- 2007-12-11 CN CNA2007800458130A patent/CN101589052A/zh active Pending
- 2007-12-11 US US12/518,663 patent/US8802891B2/en not_active Expired - Fee Related
- 2007-12-11 CA CA002671308A patent/CA2671308A1/en not_active Abandoned
- 2007-12-11 EP EP07848053.0A patent/EP2125842B1/en not_active Not-in-force
- 2007-12-11 JP JP2009540747A patent/JP5635263B2/ja not_active Expired - Fee Related
- 2007-12-11 CN CN201410663113.XA patent/CN104530123A/zh active Pending
- 2007-12-11 MX MX2009006160A patent/MX2009006160A/es active IP Right Grant
- 2007-12-11 PL PL07848053T patent/PL2125842T3/pl unknown
- 2007-12-11 BR BRPI0720093A patent/BRPI0720093A8/pt not_active IP Right Cessation
- 2007-12-11 WO PCT/EP2007/063682 patent/WO2008071689A2/en active Application Filing
- 2007-12-11 ES ES07848053.0T patent/ES2480945T3/es active Active
- 2007-12-11 RU RU2009125468/04A patent/RU2498989C2/ru not_active IP Right Cessation
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2014
- 2014-07-17 JP JP2014146614A patent/JP2014221812A/ja not_active Abandoned
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Also Published As
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US8802891B2 (en) | 2014-08-12 |
JP5635263B2 (ja) | 2014-12-03 |
CN104530123A (zh) | 2015-04-22 |
EP2125842A2 (en) | 2009-12-02 |
JP2010512370A (ja) | 2010-04-22 |
WO2008071689A3 (en) | 2008-10-09 |
WO2008071689A2 (en) | 2008-06-19 |
US20100174110A1 (en) | 2010-07-08 |
CA2671308A1 (en) | 2008-06-19 |
US20140336408A1 (en) | 2014-11-13 |
EP2125842B1 (en) | 2014-05-21 |
RU2498989C2 (ru) | 2013-11-20 |
RU2009125468A (ru) | 2011-01-20 |
EP1932848A1 (en) | 2008-06-18 |
ES2480945T3 (es) | 2014-07-29 |
PL2125842T3 (pl) | 2014-10-31 |
MX2009006160A (es) | 2009-06-19 |
JP2014221812A (ja) | 2014-11-27 |
BRPI0720093A8 (pt) | 2016-10-11 |
BRPI0720093A2 (pt) | 2013-12-24 |
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