DK3149014T3 - Fremgangsmåde til fremstilling af krystallinsk dtpmp - Google Patents
Fremgangsmåde til fremstilling af krystallinsk dtpmp Download PDFInfo
- Publication number
- DK3149014T3 DK3149014T3 DK15729105.5T DK15729105T DK3149014T3 DK 3149014 T3 DK3149014 T3 DK 3149014T3 DK 15729105 T DK15729105 T DK 15729105T DK 3149014 T3 DK3149014 T3 DK 3149014T3
- Authority
- DK
- Denmark
- Prior art keywords
- dtpmp
- mass
- crude product
- acid
- crystal modification
- Prior art date
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- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 title claims description 215
- 238000000034 method Methods 0.000 title claims description 108
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000013078 crystal Substances 0.000 claims description 191
- 230000004048 modification Effects 0.000 claims description 123
- 238000012986 modification Methods 0.000 claims description 123
- 239000002253 acid Substances 0.000 claims description 102
- 239000007787 solid Substances 0.000 claims description 101
- 230000008569 process Effects 0.000 claims description 78
- 239000012043 crude product Substances 0.000 claims description 73
- 239000000047 product Substances 0.000 claims description 40
- 239000012535 impurity Substances 0.000 claims description 21
- 239000002002 slurry Substances 0.000 claims description 19
- 238000001914 filtration Methods 0.000 claims description 18
- 238000002441 X-ray diffraction Methods 0.000 claims description 14
- 238000010586 diagram Methods 0.000 claims description 13
- 230000005855 radiation Effects 0.000 claims description 10
- 238000004062 sedimentation Methods 0.000 claims description 5
- 229910002483 Cu Ka Inorganic materials 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 238000009210 therapy by ultrasound Methods 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- 239000002245 particle Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 37
- 238000002425 crystallisation Methods 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 239000007864 aqueous solution Substances 0.000 description 32
- 239000000725 suspension Substances 0.000 description 30
- 238000001035 drying Methods 0.000 description 26
- 239000000126 substance Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000005119 centrifugation Methods 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 17
- 238000000746 purification Methods 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000010899 nucleation Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 238000005406 washing Methods 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 13
- 238000001556 precipitation Methods 0.000 description 13
- 238000000926 separation method Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 150000004682 monohydrates Chemical class 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- -1 aminoalkylene phosphonic acids Chemical class 0.000 description 7
- 238000009792 diffusion process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 235000011007 phosphoric acid Nutrition 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000003926 complexometric titration Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000000717 retained effect Effects 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- 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 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000001694 spray drying Methods 0.000 description 4
- 238000002479 acid--base titration Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 150000004683 dihydrates Chemical class 0.000 description 3
- 239000008241 heterogeneous mixture Substances 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 238000001000 micrograph Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000006911 nucleation Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 238000005496 tempering Methods 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 238000004679 31P NMR spectroscopy Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004868 gas analysis Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- GTTBQSNGUYHPNK-UHFFFAOYSA-N hydroxymethylphosphonic acid Chemical compound OCP(O)(O)=O GTTBQSNGUYHPNK-UHFFFAOYSA-N 0.000 description 2
- 230000033001 locomotion Effects 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical class [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 238000005453 pelletization Methods 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 229940120146 EDTMP Drugs 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- RCXMQNIDOFXYDO-UHFFFAOYSA-N [4,7,10-tris(phosphonomethyl)-1,4,7,10-tetrazacyclododec-1-yl]methylphosphonic acid Chemical compound OP(O)(=O)CN1CCN(CP(O)(O)=O)CCN(CP(O)(O)=O)CCN(CP(O)(O)=O)CC1 RCXMQNIDOFXYDO-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000001461 argentometric titration Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000407 epitaxy Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000002332 oil field water Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 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
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010900 secondary nucleation Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000010942 self-nucleation Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- 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)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Claims (12)
1. Krystallisat af den rene syre DTPMP ifølge den generelle formel (I) eller en tautomer form deraf:
hvor n er et tal mellem 0 og 2, kendetegnet ved, at krystallisatet har mindst en krystalmodificering valgt fra a, β og y, hvor σ-krystalmodificeringen er kendetegnet ved følgende karakteristiske reflektioner i røntgendiffraktionsdiagrammet, målt under anvendelse af Cu-Ka stråling:
hvor jS-krystalmodificeringen er kendetegnet ved følgende karakteristiske reflektioner i røntgendiffraktionsdiagrammet, målt under anvendelse af Cu-Ka stråling:
og hvor y-krystalmodificeringen er kendetegnet ved følgende karakteristiske reflektioner i røntgendiffraktionsdiagrammet, målt under anvendelse af Cu-Ka stråling:
2. Fremgangsmåde til at opnå faststof af krystallinsk DTPMP som en ren syre med den generelle formel (I) ifølge det foregående krav fra et vandigt råprodukt, indeholdende DTPMP med en pH-værdi på mindre end 4 med følgende trin: a. at anbringe podekrystaller, indeholdende DTPMP, i et vandigt råprodukt, indeholdende DTPMP med et samlet indhold i området fra 10 til 65 ma.%, op til en opslæmningstykkelse på mellem 1 til 25%,
b. at indføre kinetisk energi i det vandige råprodukt, hvorved et krystallisat, indeholdende DTPMP som en ren syre med et samlet indhold på mindst 75 ma.%, udfældes, c. at separere krystallisatet fra det vandige råprodukt ved hjælp af sedimentering og/eller filtrering.
3. Fremgangsmåde ifølge krav 2, kendetegnet ved, at det vandige råprodukt indeholder urenheder i form af biprodukter og/eller ikke-omsatte udgangsprodukter.
4. Fremgangsmåde ifølge krav 2 eller krav 3, kendetegnet ved, at den kinetiske energi indføres i form af omrøring og/eller rystning og/eller ultrasonisk behandling.
5. Fremgangsmåde ifølge kravene 2 til 4, kendetegnet ved, at, for at opnå et faststof, har det vandige råprodukt en temperatur i området fra 25 til 85°C.
6. Fremgangsmåde ifølge et hvilket som helst af kravene 2 til 5, kendetegnet ve, at et separeret krystallisat har et faststofindhold på mindst 65%.
7. Fremgangsmåde ifølge et hvilket som helst af kravene 2 til 6, kendetegnet ved, at fremgangsmåden omfatter mindst et isotermisk procestrin, hvor temperaturforskellen i det vandige råprodukt er konstant i løbet af et defineret tidsrum for introduktion af kinetisk energi.
8. Fremgangsmåde ifølge krav 7, kendetegnet ved, at temperaturen af det vandige råprodukt reduceres mellem det definerede tidsrum på to isotermiske procestrin med en temperaturprofil på fra 1 til 7 K per dag.
9. Fremgangsmåde ifølge et hvilket som helst af kravene 2 til 8, kendetegnet ved, at fremgangsmåden udføres i en kvasikontinuerlig drift.
10. Fremgangsmåde ifølge et hvilket som helst af kravene 2 til 6, kendetegnet ved, at, for at opnå et faststof, har det vandige råprodukt en stærk syre i området fra 1 til 4,5 ma.%.
11. Anvendelse af en fremgangsmåde ifølge et hvilket som helst af kravene 2 til 10 til oprensning af et vandholdigt råprodukt, indeholdende DTPMP, med et samlet indhold på mindst 10 ma.%.
12. Anvendelse af en fremgangsmåde ifølge et hvilket som helst af kravene 2 til 6 til fremstilling af et krystallisat af den rene syre DTPMP ifølge den generelle formel (I) ifølge krav 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102014210377 | 2014-06-02 | ||
| PCT/EP2015/062252 WO2015185548A1 (de) | 2014-06-02 | 2015-06-02 | Verfahren zur herstellung kristalliner dtpmp |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3149014T3 true DK3149014T3 (da) | 2019-04-29 |
Family
ID=54481748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK15729105.5T DK3149014T3 (da) | 2014-06-02 | 2015-06-02 | Fremgangsmåde til fremstilling af krystallinsk dtpmp |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10590153B2 (da) |
| EP (1) | EP3149014B1 (da) |
| CN (2) | CN115974917A (da) |
| DE (1) | DE102015210145A1 (da) |
| DK (1) | DK3149014T3 (da) |
| ES (1) | ES2721030T3 (da) |
| PL (1) | PL3149014T3 (da) |
| PT (1) | PT3149014T (da) |
| TR (1) | TR201905374T4 (da) |
| WO (1) | WO2015185548A1 (da) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477390A (en) | 1981-08-21 | 1984-10-16 | Monsanto Company | Aminomethylenephosphonic acid solutions |
| 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 |
| GB8308003D0 (en) * | 1983-03-23 | 1983-04-27 | Albright & Wilson | Phosphonates |
| EP0225409A1 (en) * | 1985-12-02 | 1987-06-16 | The Dow Chemical Company | Organic amine phosphonic acid complexes for the treatment of calcific tumors |
| US4937333A (en) | 1989-08-04 | 1990-06-26 | The Dow Chemical Company | Method for purifying aminomethylenephosphonic acids for pharmaceutical use |
| DE69027828T2 (de) | 1989-10-13 | 1996-11-21 | Fujitsu Ltd | Integrierte Halbleiter-Schaltungs-Vorrichtungen |
| US5495042A (en) | 1993-11-04 | 1996-02-27 | Cytogen Corporation | Non-alkaline purification of aminophosphonic acids |
| JP2002105089A (ja) * | 2000-09-25 | 2002-04-10 | Mitsubishi Gas Chem Co Inc | アミノホスホン酸の精製方法 |
| EP1681294A1 (en) | 2005-01-17 | 2006-07-19 | Solutia Europe N.V./S.A. | Process for the manufacture of aminopolyalkylene-phosphonic acid compounds |
| CN100471860C (zh) * | 2007-02-13 | 2009-03-25 | 山东省泰和水处理有限公司 | 一种适用于电子级固体氨基三亚甲基膦酸的制备工艺 |
| CN101381376B (zh) * | 2008-10-23 | 2011-06-15 | 山东省泰和水处理有限公司 | 一种适用于电子级固体乙二胺四亚甲基膦酸的制备工艺 |
| US20120136171A1 (en) | 2009-05-28 | 2012-05-31 | Straitmark Holding Ag | Method for the manufacture ofamino alkylene phosphonic acids |
| RU2434875C1 (ru) * | 2010-04-12 | 2011-11-27 | Федеральное Государственное Унитарное Предприятие "Государственный Ордена Трудового Красного Знамени Научно-Исследовательский Институт Химических Реактивов И Особо Чистых Химических Веществ" | Способ получения полиалкиленполиаминполиметилфосфоновых кислот |
-
2015
- 2015-06-02 DK DK15729105.5T patent/DK3149014T3/da active
- 2015-06-02 TR TR2019/05374T patent/TR201905374T4/tr unknown
- 2015-06-02 DE DE102015210145.2A patent/DE102015210145A1/de not_active Withdrawn
- 2015-06-02 CN CN202211007857.7A patent/CN115974917A/zh active Pending
- 2015-06-02 CN CN201580041776.0A patent/CN106661062A/zh active Pending
- 2015-06-02 PT PT15729105T patent/PT3149014T/pt unknown
- 2015-06-02 ES ES15729105T patent/ES2721030T3/es active Active
- 2015-06-02 PL PL15729105T patent/PL3149014T3/pl unknown
- 2015-06-02 EP EP15729105.5A patent/EP3149014B1/de active Active
- 2015-06-02 US US15/315,841 patent/US10590153B2/en active Active
- 2015-06-02 WO PCT/EP2015/062252 patent/WO2015185548A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| TR201905374T4 (tr) | 2019-05-21 |
| CN106661062A (zh) | 2017-05-10 |
| US20170101426A1 (en) | 2017-04-13 |
| ES2721030T8 (es) | 2019-08-19 |
| DE102015210145A1 (de) | 2015-12-03 |
| PT3149014T (pt) | 2019-05-06 |
| WO2015185548A1 (de) | 2015-12-10 |
| ES2721030T3 (es) | 2019-07-26 |
| PL3149014T3 (pl) | 2019-08-30 |
| US10590153B2 (en) | 2020-03-17 |
| EP3149014B1 (de) | 2019-01-30 |
| CN115974917A (zh) | 2023-04-18 |
| EP3149014A1 (de) | 2017-04-05 |
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