1116:
1143:
1087:
162:
1170:
1058:
941:
1033:
1807:
20:
396:
154:
848:
447:
2156:
843:{\displaystyle {\begin{aligned}{\ce {2 H3PO4}}&\longrightarrow {\ce {H4P2O7 + H2O}}\\{\ce {H4P2O7 + H3PO4}}&\longrightarrow {\ce {H5P3O10 + H2O}}\\{\ce {H5P3O10 + H3PO4}}&\longrightarrow {\ce {H6P4O13 + H2O}}\end{aligned}}}
2070:"Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates"
452:
1691:
Conversely, polyphosphoric acids or polyphosphates are often formed by dehydrating a phosphoric acid solution; in other words, removing water from it often by heating and evaporating the water off.
1791:
ions to form anions, again depending on the pH in a solution. In the biochemistry of living organisms, there are many kinds of (mono)phosphate, diphosphate, and triphosphate compounds (essentially
1195:
1744:
3608:
3719:
3711:
3656:
3552:
1771:
groups, it can esterify with one, two, or three alcohol molecules to form a mono-, di-, or triester. See the general structure image of an ortho- (or mono-) phosphate
3396:
3075:
3648:
3632:
3616:
1684:
polyphosphates into smaller phosphates and finally into ortho-phosphate, given enough water. Higher temperature or acidic conditions can speed up the hydrolysis
3727:
3640:
3560:
3436:
3328:
2154:, Young, Donald C., "Production of ammonium phosphates and product thereof", published 1962-07-17, assigned to Collier Carbon & Chemical Co.
440:
2145:
1497:, and so on. Note that each extra phosphoric unit adds one extra P atom, three extra O atoms, and either one extra hydrogen atom or an extra negative charge.
3240:
852:
The "backbone" of a polyphosphoric acid molecule is a chain of alternating P and O atoms. Each extra orthophosphoric unit that is condensed adds 1 extra H (
3228:
3064:
3677:
3365:
3312:
2832:
2307:
3377:
2113:
2185:
1960:
Eaton, P. E.; Carlson, G. R.; Lee, J. T. (1973). "Phosphorus pentoxide-methanesulfonic acid. Convenient alternative to polyphosphoric acid".
3792:
932:) is a colorless, vitreous, deliquescent solid, density 2.2 to 2.5 g/cc, which sublimes upon heating. It is soluble in ethanol.
2146:
Determination of
Polyphosphates Using Ion Chromatography with Suppressed Conductivity Detection, Application Note 71 by Dionex
2780:
1115:
1026:
in the molecule's structure; that is, the minimum number of bonds that would have to be broken to eliminate all cycles.
2178:
1086:
1732:
1142:
1169:
1057:
1735:. As a corrosion inhibitor, polyphosphates work by forming a protective film on the interior surface of pipes.
1200:
The limiting case of internal condensation, where all oxygen atoms are shared and there are no hydrogen atoms (
2171:
1500:
Branched polyphosphoric acids give similarly branched polyphosphate anions. The simplest example of this is
1032:
3777:
1869:
1569:
Salts or esters of cyclic polyphosphoric acids are often called "metaphosphates". What are commonly called
1272:
turns a phosphoric acid into a phosphate anion. Partial removal yields various hydrogen phosphate anions.
3568:
2441:
948:
Phosphoric acid units can be bonded together in rings (cyclic structures). The simplest such compound is
2017:
2663:
2614:
2151:
3772:
3624:
3584:
2128:
971:. Its structure is shown in the illustration. Since the ends are condensed, its formula has one less
3576:
3106:
2773:
2716:
2634:
2606:
2350:
1844:
1606:
3787:
3669:
3600:
3592:
3339:
3091:
3083:
3034:
2740:
2590:
2582:
2466:
2391:
2365:
2287:
1849:
1829:
1747:
General chemical structure of a monophosphate ester; here any R can be H or some organic radical.
1704:
3258:
3012:
2962:
2895:
2814:
2658:
2626:
2598:
2503:
2436:
2355:
1839:
1811:
1800:
1672:
start becoming less soluble and phosphate salts of various other metals are even less soluble.
1501:
1314:
3023:
2574:
2553:
2415:
2215:
1834:
1796:
1557:. Generally in an aqueous solution, the degree or percentage of dissociation depends on the
3696:
3169:
3153:
3137:
3046:
2950:
2880:
2817:
2704:
2692:
2642:
2426:
2292:
2277:
2194:
1894:
Harwood, Laurence M.; Hodgkinson, Leslie C.; Sutherland, James K.; Towers, Patrick (1984).
1329:
1244:
1175:
8:
3782:
3425:
3346:
3266:
3129:
2978:
2928:
2766:
2680:
2675:
2548:
2523:
2476:
2451:
2386:
2381:
2331:
2302:
1896:"Synthesis of anthracyclinones. Part 1. Regioselective alkylation of 5-hydroxyquinizarin"
1728:
1063:
428:
165:
3448:
3114:
2939:
2918:
2865:
2728:
2461:
2456:
2405:
2345:
2210:
1518:
The general formula for such (non-cyclic) polyphosphate anions, linear or branched, is
1092:
914:
434:
1680:
In aqueous solutions (solutions of water), water gradually (over the course of hours)
1573:
actually have a mixture of ring sizes. A general formula for such cyclic compounds is
3464:
3201:
2992:
2518:
2513:
2488:
2376:
2336:
2321:
2316:
2256:
2244:
2230:
2225:
2091:
2039:
1685:
1654:
902:
336:
308:
that result when one or more of the hydrogens are replaced by bonds to other groups.
301:
3300:
2910:
2854:
2528:
2493:
2326:
2282:
2268:
2081:
1970:
1940:
1907:
1456:
412:
312:
305:
161:
1707:. Sometimes pyrophosphate, tripolyphosphate, tetrapolyphosphate, etc. are called
3215:
2847:
2803:
2220:
1945:
1928:
1864:
1859:
1854:
1780:
1764:
1720:
1038:
364:
357:
75:
44:
36:
16:
Class of chemical species; phosphorus oxoacids and their deprotonated derivatives
940:
319:, include some of the best-known compounds of phosphorus, of high importance in
3185:
2536:
2297:
1874:
1756:
1666:
332:
183:
70:
tetrahedra may be connected by shared single-bonded oxygens, forming linear or
3766:
2999:
1962:
1929:"Studies on the Application of Polyphosphoric Acid as a Condensing Agent. II"
1629:
1400:
1356:
48:
1783:. Di- and tripoly- (or tri-) phosphate esters, etc. are also possible. Any
2095:
1724:
1194:
408:
320:
1806:
1699:
Ortho-, pyro-, and tripolyphosphate compounds have been commonly used in
1625:
1023:
906:
328:
128:
79:
60:
56:
19:
1974:
423:. (However, the distinction between the two terms is not well defined.)
2163:
1681:
857:
324:
71:
40:
2086:
2069:
395:
362:
The simplest and most commonly encountered of the phosphoric acids is
153:
2789:
2650:
2202:
1700:
1298:
1281:
1224:
910:
383:
often means this compound specifically (and this is also the current
340:
28:
2068:
Parmar, Dixit; Sugiono, Erli; Raja, Sadiya; Rueping, Magnus (2014).
1959:
1912:
1895:
1760:
1658:
853:
404:
86:
2006:. New York: The Interscience Encyclopedia, Inc. 1953. p. 421.
1743:
1893:
1650:
1795:), many of which play a significant role in metabolism such as
1662:
1266:
861:
172:
52:
2758:
1815:
1792:
1772:
1669:
1646:
1598:
384:
316:
187:
2047:
Government
Engineering:The Journal for Public Infrastructure
1605:
are formed. An example of a compound with such an anion is
1350:
1787:
groups on the phosphates in these ester molecules may lose
390:
83:
1927:
Nakazawa, Koichi; Matsuura, Shin; Kusuda, Kosuke (1954).
1485:
yields at least six anions, including tetrapolyphosphate
864:) atoms. The general formula of a polyphosphoric acid is
829:
813:
800:
787:
765:
752:
736:
723:
710:
688:
672:
659:
646:
624:
611:
595:
582:
569:
547:
531:
518:
505:
483:
470:
2111:
2067:
1991:(49 ed.). Chemical Rubber Co. 1968. p. B-226.
1558:
1926:
1755:
groups in phosphoric acids can also condense with the
1703:(i. e. cleaners) formulations. For example, see
2112:
Schröder HC, Kurz L, Muller WE, Lorenz B (Mar 2000).
450:
82:
oxygen atoms that are not shared are completed with
89:atoms. The general formula of a phosphoric acid is
1593:When metaphosphoric acids lose their hydrogens as
842:
1665:phosphates are also quite soluble in water. The
3764:
2018:"Polyphosphates for scale and corrosion control"
1414:. The pyrophosphates are mostly water-soluble.
1675:
1590:= number of phosphoric units in the molecule.
2774:
2179:
1645:These phosphoric acids series are generally
982:The general formula of a phosphoric acid is
131:in the molecule's structure, between 0 and
2781:
2767:
2186:
2172:
2040:"Ortho-Polyphosphate Corrosion Inhibitors"
935:
2085:
1944:
1911:
1719:, etc., especially when they are part of
1351:Linear oligophosphates and polyphosphates
459:
415:. Condensation of a few units yields the
2193:
1805:
1742:
1564:
1515:and its partially dissociated versions.
939:
411:into larger molecules by elimination of
394:
391:Oligophosphoric and polyphosphoric acids
160:
152:
18:
1767:. Since orthophosphoric acid has three
444:acids can be obtained by the reactions
3765:
2822:
1635:
1018:is the number of phosphorus atoms and
920:
123:is the number of phosphorus atoms and
3541:
2762:
2167:
2150:
1301:(commonly called simply "phosphate")
979:(water) than tripolyphosphoric acid.
300:. The term phosphate is also used in
1989:CRC Handbook of Chemstry and Physics
1775:below on the left, where any of the
1399:ranges from 1 to 4. The last one is
1361:Dissociation of pyrophosphoric acid
419:, while larger molecules are called
2004:Encyclopedia of Chemical Technology
1738:
1727:. They are also used for scale and
1286:The anions of orthophosphoric acid
13:
2105:
2002:"Phosphoric acid and phosphates".
351:
78:, or more complex structures. The
14:
3804:
2139:
1417:Likewise, tripolyphosphoric acid
1275:
1265:Removal of the hydrogen atoms as
901:Polyphosphoric acids are used in
403:Two or more orthophosphoric acid
311:These acids, together with their
55:(O) atoms, one of them through a
2049:(September–October, 2006): 48–49
1193:
1168:
1141:
1114:
1085:
1056:
1031:
263:. The fully dissociated anion (
1779:groups can be a hydrogen or an
59:, arranged as the corners of a
3793:Reagents for organic chemistry
2788:
2061:
2032:
2010:
1995:
1981:
1953:
1920:
1887:
1455:ranges from 1 to 5, including
773:
632:
491:
35:, in the general sense, is a
1:
2020:. Tramfloc, INC. January 2009
1900:Canadian Journal of Chemistry
1881:
1640:
1260:
2127:(3): 296–303. Archived from
1946:10.1248/yakushi1947.74.5_495
1870:Ribonucleoside monophosphate
1432:yields at least five anions
7:
1822:
1797:adenosine diphosphate (ADP)
1676:Hydrolysis and condensation
1470:. Tetrapolyphosphoric acid
10:
3811:
3543:
1354:
1279:
355:
2824:
2796:
2567:
2201:
166:Trimethyl orthophosphate.
1845:Adenosine tetraphosphate
1607:sodium hexametaphosphate
1121:Tetrapolyphosphoric acid
954:cyclo-triphosphoric acid
346:
228:), with general formula
2114:"Polyphosphate in bone"
1850:Nucleoside triphosphate
1830:Adenosine monophosphate
1733:potable water providers
1705:Sodium tripolyphosphate
1694:
1376:generates four anions,
936:Cyclic phosphoric acids
860:) atom, and 3 extra O (
63:. Two or more of these
1840:Adenosine triphosphate
1819:
1812:chiral phosphoric acid
1748:
1502:triphosphono phosphate
1315:monohydrogen phosphate
1148:Trimetaphosphoric acid
1093:Tripolyphosphoric acid
950:trimetaphosphoric acid
945:
944:Trimetaphosphoric acid
844:
400:
168:
158:
24:
2121:Biochemistry (Moscow)
1835:Adenosine diphosphate
1809:
1746:
1565:Cyclic polyphosphates
943:
925:Metaphosphoric acid (
845:
417:oligophosphoric acids
398:
164:
156:
22:
2195:Phosphorus compounds
1330:dihydrogen phosphate
1245:phosphorus pentoxide
1176:Phosphoric anhydride
1039:Orthophosphoric acid
913:; an alternative is
890:HO[−P(O)(OH)−O−]
448:
421:polyphosphoric acids
365:orthophosphoric acid
157:Pyrophosphate anion.
23:Pyrophosphoric acid.
3778:Inorganic compounds
1975:10.1021/jo00987a028
1657:of the molecules.
1636:Chemical properties
1550:may vary from 1 to
1546:, where the charge
1395:, where the charge
1064:Pyrophosphoric acid
956:having the formula
921:Metaphosphoric acid
856:) atom, 1 extra P (
831:
815:
802:
789:
767:
754:
738:
725:
712:
690:
674:
661:
648:
626:
613:
597:
584:
571:
549:
533:
520:
507:
485:
472:
399:Polyphosphoric acid
379:. Indeed, the term
211:hydrogen phosphates
190:generically called
43:(P) atom is in the
1820:
1801:triphosphate (ATP)
1749:
1024:fundamental cycles
946:
840:
838:
819:
803:
790:
777:
755:
742:
726:
713:
700:
678:
662:
649:
636:
614:
601:
585:
572:
559:
537:
521:
508:
495:
473:
460:
401:
169:
159:
129:fundamental cycles
37:phosphorus oxoacid
25:
3760:
3759:
3754:
3753:
2756:
2755:
2087:10.1021/cr5001496
2080:(18): 9047–9153.
1906:(10): 1922–1925.
1729:corrosion control
1571:trimetaphosphates
1561:of the solution.
1022:is the number of
903:organic synthesis
834:
822:
806:
793:
780:
758:
745:
729:
716:
703:
693:
681:
665:
652:
639:
617:
604:
588:
575:
562:
552:
540:
524:
511:
498:
476:
463:
407:can be joined by
341:chemical research
337:chemical industry
306:functional groups
302:organic chemistry
217:is between 1 and
127:is the number of
3800:
3773:Dietary minerals
2800:
2799:
2783:
2776:
2769:
2760:
2759:
2559:
2509:
2499:
2472:
2447:
2432:
2422:
2411:
2401:
2372:
2361:
2240:
2188:
2181:
2174:
2165:
2164:
2160:
2159:
2155:
2135:
2133:
2118:
2100:
2099:
2089:
2074:Chemical Reviews
2065:
2059:
2058:
2056:
2054:
2044:
2036:
2030:
2029:
2027:
2025:
2014:
2008:
2007:
1999:
1993:
1992:
1985:
1979:
1978:
1957:
1951:
1950:
1948:
1924:
1918:
1917:
1915:
1891:
1790:
1786:
1770:
1765:phosphate esters
1754:
1739:Phosphate esters
1721:phosphate esters
1653:considering the
1623:
1596:
1585:
1556:
1545:
1514:
1496:
1484:
1469:
1457:tripolyphosphate
1450:
1431:
1413:
1394:
1375:
1346:
1345:
1344:
1341:
1327:
1326:
1325:
1322:
1312:
1311:
1310:
1307:
1296:
1271:
1256:
1242:
1222:
1220:
1219:
1216:
1213:
1197:
1188:
1172:
1163:
1145:
1136:
1118:
1109:
1089:
1080:
1060:
1051:
1035:
1013:
978:
970:
931:
897:
887:
849:
847:
846:
841:
839:
835:
832:
830:
827:
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811:
804:
801:
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791:
788:
785:
778:
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766:
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750:
743:
737:
734:
727:
724:
721:
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673:
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637:
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567:
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550:
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538:
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522:
519:
516:
509:
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503:
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484:
481:
474:
471:
468:
461:
378:
299:
277:
262:
227:
208:
178:
149:
147:
146:
143:
140:
118:
69:
3810:
3809:
3803:
3802:
3801:
3799:
3798:
3797:
3763:
3762:
3761:
3756:
3755:
3731:
3723:
3715:
3704:
3700:
3689:
3685:
3681:
3673:
3660:
3652:
3644:
3636:
3628:
3620:
3612:
3604:
3596:
3588:
3580:
3572:
3564:
3556:
3468:
3460:
3456:
3452:
3444:
3440:
3429:
3400:
3389:
3385:
3381:
3373:
3369:
3350:
3345:
3343:
3332:
3324:
3320:
3316:
3308:
3304:
3278:
3274:
3270:
3262:
3252:
3248:
3244:
3236:
3232:
3205:
3197:
3193:
3189:
3181:
3177:
3173:
3165:
3161:
3157:
3149:
3145:
3141:
3133:
3128:
3126:
3122:
3118:
3110:
3105:
3103:
3099:
3095:
3087:
3079:
3068:
3058:
3054:
3050:
3042:
3038:
3033:
3031:
3027:
3022:
3020:
3016:
2998:
2996:
2982:
2974:
2970:
2966:
2958:
2954:
2949:
2947:
2943:
2938:
2936:
2932:
2909:
2907:
2903:
2899:
2894:
2892:
2888:
2884:
2879:
2877:
2873:
2869:
2858:
2853:
2851:
2840:
2836:
2816:
2813:
2811:
2807:
2792:
2787:
2757:
2752:
2748:
2744:
2736:
2732:
2724:
2720:
2712:
2708:
2700:
2696:
2688:
2684:
2671:
2667:
2654:
2646:
2638:
2630:
2622:
2618:
2610:
2602:
2594:
2586:
2578:
2568:Other compounds
2563:
2558:
2554:
2544:
2540:
2532:
2508:
2504:
2498:
2494:
2484:
2480:
2471:
2467:
2446:
2442:
2431:
2427:
2420:
2416:
2410:
2406:
2400:
2396:
2392:
2370:
2366:
2360:
2356:
2340:
2311:
2272:
2264:
2260:
2252:
2248:
2239:
2235:
2231:
2197:
2192:
2157:
2142:
2131:
2116:
2108:
2106:Further reading
2103:
2066:
2062:
2052:
2050:
2042:
2038:
2037:
2033:
2023:
2021:
2016:
2015:
2011:
2001:
2000:
1996:
1987:
1986:
1982:
1958:
1954:
1933:Yakugaku Zasshi
1925:
1921:
1913:10.1139/v84-329
1892:
1888:
1884:
1879:
1865:Phosphoramidate
1860:Phosphonic acid
1855:Organophosphate
1825:
1810:Structure of a
1788:
1784:
1781:organic radical
1768:
1757:hydroxyl groups
1752:
1741:
1697:
1678:
1643:
1638:
1622:
1618:
1614:
1610:
1594:
1584:
1578:
1574:
1567:
1551:
1543:
1535:
1529:
1519:
1512:
1508:
1504:
1494:
1490:
1486:
1483:
1479:
1475:
1471:
1467:
1463:
1459:
1448:
1444:
1440:
1433:
1430:
1426:
1422:
1418:
1411:
1407:
1403:
1392:
1388:
1384:
1377:
1374:
1370:
1366:
1362:
1359:
1353:
1342:
1339:
1338:
1336:
1332:
1323:
1320:
1319:
1317:
1308:
1305:
1304:
1302:
1295:
1291:
1287:
1284:
1278:
1269:
1263:
1255:
1251:
1247:
1241:
1234:
1227:
1217:
1214:
1208:
1207:
1205:
1189:
1187:
1183:
1179:
1178:
1173:
1164:
1162:
1158:
1154:
1150:
1149:
1146:
1137:
1135:
1131:
1127:
1123:
1122:
1119:
1110:
1108:
1104:
1100:
1096:
1095:
1090:
1081:
1079:
1075:
1071:
1067:
1066:
1061:
1052:
1050:
1046:
1042:
1041:
1036:
1012:
1000:
994:
983:
976:
972:
969:
965:
961:
957:
938:
930:
926:
923:
915:Eaton's reagent
895:
889:
886:
878:
872:
865:
837:
836:
828:
823:
812:
807:
799:
794:
786:
781:
776:
769:
764:
759:
751:
746:
735:
730:
722:
717:
709:
704:
699:
696:
695:
687:
682:
671:
666:
658:
653:
645:
640:
635:
628:
623:
618:
610:
605:
594:
589:
581:
576:
568:
563:
558:
555:
554:
546:
541:
530:
525:
517:
512:
504:
499:
494:
487:
482:
477:
469:
464:
455:
451:
449:
446:
445:
441:tetraphosphoric
393:
387:nomenclature).
381:phosphoric acid
377:
373:
369:
360:
358:Phosphoric acid
354:
352:Phosphoric acid
349:
297:
285:
279:
264:
260:
249:
243:
229:
218:
195:
184:hydroxyl groups
176:
144:
141:
135:
134:
132:
117:
106:
100:
90:
72:branched chains
68:
64:
45:oxidation state
33:phosphoric acid
17:
12:
11:
5:
3808:
3807:
3796:
3795:
3790:
3788:Pyrophosphates
3785:
3780:
3775:
3758:
3757:
3752:
3751:
3748:
3745:
3742:
3739:
3736:
3733:
3729:
3725:
3721:
3717:
3713:
3709:
3706:
3702:
3698:
3694:
3691:
3687:
3683:
3679:
3675:
3671:
3667:
3663:
3662:
3658:
3654:
3650:
3646:
3642:
3638:
3634:
3630:
3626:
3622:
3618:
3614:
3610:
3606:
3602:
3598:
3594:
3590:
3586:
3582:
3578:
3574:
3570:
3566:
3562:
3558:
3554:
3550:
3546:
3545:
3542:
3539:
3538:
3535:
3532:
3529:
3526:
3523:
3520:
3517:
3514:
3511:
3508:
3505:
3502:
3499:
3496:
3493:
3490:
3487:
3484:
3480:
3479:
3476:
3473:
3470:
3466:
3462:
3458:
3454:
3450:
3446:
3442:
3438:
3434:
3431:
3427:
3423:
3420:
3417:
3414:
3411:
3408:
3405:
3402:
3398:
3394:
3391:
3387:
3383:
3379:
3375:
3371:
3367:
3362:
3361:
3358:
3355:
3352:
3348:
3341:
3337:
3334:
3330:
3326:
3322:
3318:
3314:
3310:
3306:
3302:
3298:
3295:
3292:
3289:
3286:
3283:
3280:
3276:
3272:
3268:
3264:
3260:
3256:
3254:
3250:
3246:
3242:
3238:
3234:
3230:
3225:
3224:
3221:
3218:
3213:
3210:
3207:
3203:
3199:
3195:
3191:
3187:
3183:
3179:
3175:
3171:
3167:
3163:
3159:
3155:
3151:
3147:
3143:
3139:
3135:
3131:
3124:
3120:
3116:
3112:
3108:
3101:
3097:
3093:
3089:
3085:
3081:
3077:
3073:
3070:
3066:
3062:
3060:
3056:
3052:
3048:
3044:
3040:
3036:
3029:
3025:
3018:
3014:
3009:
3008:
3005:
3002:
2994:
2990:
2987:
2984:
2980:
2976:
2972:
2968:
2964:
2960:
2956:
2952:
2945:
2941:
2934:
2930:
2925:
2924:
2921:
2916:
2913:
2905:
2901:
2897:
2890:
2886:
2882:
2875:
2871:
2867:
2863:
2860:
2856:
2849:
2845:
2842:
2838:
2834:
2829:
2828:
2825:
2823:
2821:
2819:
2809:
2805:
2798:
2797:
2794:
2793:
2786:
2785:
2778:
2771:
2763:
2754:
2753:
2751:
2750:
2746:
2742:
2738:
2734:
2730:
2726:
2722:
2718:
2714:
2710:
2706:
2702:
2698:
2694:
2690:
2686:
2682:
2678:
2673:
2669:
2665:
2661:
2656:
2652:
2648:
2644:
2640:
2636:
2632:
2628:
2624:
2620:
2616:
2612:
2608:
2604:
2600:
2596:
2592:
2588:
2584:
2580:
2576:
2571:
2569:
2565:
2564:
2562:
2561:
2556:
2551:
2546:
2542:
2538:
2534:
2530:
2526:
2521:
2516:
2511:
2506:
2501:
2496:
2491:
2486:
2482:
2478:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2418:
2413:
2408:
2403:
2398:
2394:
2389:
2384:
2379:
2374:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2334:
2329:
2324:
2319:
2314:
2309:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2266:
2262:
2258:
2254:
2250:
2246:
2242:
2237:
2233:
2228:
2223:
2218:
2213:
2207:
2205:
2199:
2198:
2191:
2190:
2183:
2176:
2168:
2162:
2161:
2148:
2141:
2140:External links
2138:
2137:
2136:
2134:on 2011-08-25.
2107:
2104:
2102:
2101:
2060:
2031:
2009:
1994:
1980:
1952:
1939:(5): 495–497.
1919:
1885:
1883:
1880:
1878:
1877:
1875:Superphosphate
1872:
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1832:
1826:
1824:
1821:
1740:
1737:
1717:tetraphosphate
1696:
1693:
1688:considerably.
1677:
1674:
1667:alkaline earth
1642:
1639:
1637:
1634:
1620:
1616:
1612:
1603:metaphosphates
1580:
1576:
1566:
1563:
1537:
1531:
1521:
1510:
1506:
1492:
1488:
1481:
1477:
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1446:
1442:
1435:
1428:
1424:
1420:
1409:
1405:
1390:
1386:
1379:
1372:
1368:
1364:
1355:Main article:
1352:
1349:
1334:
1299:orthophosphate
1293:
1289:
1280:Main article:
1277:
1276:Orthophosphate
1274:
1262:
1259:
1253:
1249:
1236:
1229:
1191:
1190:
1185:
1181:
1174:
1167:
1165:
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1152:
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985:
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928:
922:
919:
891:
880:
874:
867:
826:
818:
810:
797:
784:
775:
772:
770:
762:
749:
741:
733:
720:
707:
698:
697:
685:
677:
669:
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634:
631:
629:
621:
608:
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579:
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556:
544:
536:
528:
515:
502:
493:
490:
488:
480:
467:
458:
454:
453:
429:pyrophosphoric
392:
389:
375:
371:
356:Main article:
353:
350:
348:
345:
287:
281:
278:) has formula
251:
245:
231:
108:
102:
92:
66:
39:in which each
15:
9:
6:
4:
3:
2:
3806:
3805:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3770:
3768:
3749:
3746:
3743:
3740:
3737:
3734:
3732:
3726:
3724:
3718:
3716:
3710:
3707:
3705:
3695:
3692:
3690:
3676:
3674:
3668:
3665:
3664:
3661:
3655:
3653:
3647:
3645:
3639:
3637:
3631:
3629:
3623:
3621:
3615:
3613:
3607:
3605:
3599:
3597:
3591:
3589:
3583:
3581:
3575:
3573:
3567:
3565:
3559:
3557:
3551:
3548:
3547:
3540:
3536:
3533:
3530:
3527:
3524:
3521:
3518:
3515:
3512:
3509:
3506:
3503:
3500:
3497:
3494:
3491:
3488:
3485:
3482:
3481:
3477:
3474:
3471:
3469:
3463:
3461:
3447:
3445:
3435:
3432:
3430:
3424:
3421:
3418:
3415:
3412:
3409:
3406:
3403:
3401:
3395:
3392:
3390:
3376:
3374:
3364:
3363:
3359:
3356:
3353:
3351:
3344:
3338:
3335:
3333:
3327:
3325:
3311:
3309:
3299:
3296:
3293:
3290:
3287:
3284:
3281:
3279:
3265:
3263:
3257:
3255:
3253:
3239:
3237:
3227:
3226:
3222:
3219:
3217:
3214:
3211:
3208:
3206:
3200:
3198:
3184:
3182:
3168:
3166:
3152:
3150:
3136:
3134:
3127:
3113:
3111:
3104:
3090:
3088:
3082:
3080:
3074:
3071:
3069:
3063:
3061:
3059:
3045:
3043:
3032:
3021:
3011:
3010:
3006:
3003:
3001:
2997:
2991:
2988:
2985:
2983:
2977:
2975:
2961:
2959:
2948:
2937:
2927:
2926:
2922:
2920:
2917:
2914:
2912:
2908:
2893:
2878:
2864:
2861:
2859:
2852:
2846:
2843:
2841:
2831:
2830:
2826:
2820:
2818:
2815:
2812:
2802:
2801:
2795:
2791:
2784:
2779:
2777:
2772:
2770:
2765:
2764:
2761:
2749:
2739:
2737:
2727:
2725:
2715:
2713:
2703:
2701:
2691:
2689:
2679:
2677:
2674:
2672:
2662:
2660:
2657:
2655:
2649:
2647:
2641:
2639:
2633:
2631:
2625:
2623:
2613:
2611:
2605:
2603:
2597:
2595:
2589:
2587:
2581:
2579:
2573:
2572:
2570:
2566:
2560:
2552:
2550:
2547:
2545:
2535:
2533:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2510:
2502:
2500:
2492:
2490:
2487:
2485:
2475:
2473:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2440:
2438:
2435:
2433:
2425:
2423:
2414:
2412:
2404:
2402:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2364:
2362:
2354:
2352:
2349:
2347:
2344:
2342:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2267:
2265:
2255:
2253:
2243:
2241:
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2212:
2209:
2208:
2206:
2204:
2200:
2196:
2189:
2184:
2182:
2177:
2175:
2170:
2169:
2166:
2153:
2149:
2147:
2144:
2143:
2130:
2126:
2122:
2115:
2110:
2109:
2097:
2093:
2088:
2083:
2079:
2075:
2071:
2064:
2048:
2041:
2035:
2019:
2013:
2005:
1998:
1990:
1984:
1976:
1972:
1968:
1965:
1964:
1963:J. Org. Chem.
1956:
1947:
1942:
1938:
1934:
1930:
1923:
1914:
1909:
1905:
1901:
1897:
1890:
1886:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1827:
1817:
1814:derived from
1813:
1808:
1804:
1802:
1798:
1794:
1782:
1778:
1774:
1766:
1762:
1758:
1745:
1736:
1734:
1730:
1726:
1722:
1718:
1714:
1710:
1706:
1702:
1692:
1689:
1687:
1683:
1673:
1671:
1668:
1664:
1660:
1656:
1652:
1648:
1633:
1631:
1630:food additive
1627:
1624:), used as a
1608:
1604:
1600:
1591:
1589:
1583:
1572:
1562:
1560:
1554:
1549:
1541:
1534:
1528:
1524:
1516:
1503:
1498:
1458:
1454:
1439:
1415:
1402:
1401:pyrophosphate
1398:
1383:
1358:
1357:Polyphosphate
1348:
1331:
1316:
1300:
1283:
1273:
1268:
1258:
1246:
1240:
1233:
1226:
1211:
1203:
1198:
1196:
1177:
1171:
1166:
1144:
1139:
1117:
1112:
1094:
1088:
1083:
1065:
1059:
1054:
1040:
1034:
1029:
1028:
1027:
1025:
1021:
1017:
1010:
1006:
999:
992:
988:
980:
955:
951:
942:
933:
918:
916:
912:
908:
904:
899:
894:
884:
877:
870:
863:
859:
855:
850:
824:
816:
808:
795:
782:
771:
760:
747:
739:
731:
718:
705:
683:
675:
667:
654:
641:
630:
619:
606:
598:
590:
577:
564:
542:
534:
526:
513:
500:
489:
478:
465:
456:
443:
442:
437:
436:
435:triphosphoric
431:
430:
426:For example,
424:
422:
418:
414:
410:
406:
397:
388:
386:
382:
367:
366:
359:
344:
342:
338:
334:
330:
326:
322:
318:
314:
309:
307:
303:
295:
291:
284:
275:
271:
267:
259:
255:
248:
242:
238:
234:
225:
221:
216:
212:
206:
202:
198:
193:
189:
185:
182:
174:
167:
163:
155:
151:
138:
130:
126:
122:
116:
112:
105:
99:
95:
88:
85:
81:
80:single-bonded
77:
73:
62:
58:
54:
50:
46:
42:
38:
34:
30:
21:
2129:the original
2124:
2120:
2077:
2073:
2063:
2053:December 23,
2051:. Retrieved
2046:
2034:
2024:December 23,
2022:. Retrieved
2012:
2003:
1997:
1988:
1983:
1969:(23): 4071.
1966:
1961:
1955:
1936:
1932:
1922:
1903:
1899:
1889:
1776:
1750:
1725:biochemistry
1716:
1713:triphosphate
1712:
1708:
1698:
1690:
1679:
1644:
1602:
1592:
1587:
1581:
1570:
1568:
1552:
1547:
1539:
1532:
1526:
1522:
1517:
1499:
1452:
1437:
1416:
1396:
1381:
1360:
1285:
1264:
1238:
1231:
1209:
1201:
1199:
1192:
1019:
1015:
1008:
1004:
997:
990:
986:
981:
953:
949:
947:
924:
907:cyclizations
900:
892:
882:
875:
868:
851:
439:
433:
427:
425:
420:
416:
409:condensation
402:
380:
363:
361:
321:biochemistry
310:
293:
289:
282:
273:
269:
265:
257:
253:
246:
240:
236:
232:
223:
219:
214:
210:
204:
200:
196:
191:
180:
170:
136:
124:
120:
114:
110:
103:
97:
93:
32:
26:
1709:diphosphate
1626:sequestrant
1505:[OP(OPO
329:agriculture
186:–OH leaves
171:Removal of
61:tetrahedron
57:double bond
47:+5, and is
3783:Phosphates
3767:Categories
2790:Phosphates
2203:Phosphides
2152:US 3044851
1882:References
1701:detergents
1682:hydrolyzes
1641:Solubility
1261:Phosphates
911:acylations
858:phosphorus
325:mineralogy
192:phosphates
41:phosphorus
1686:reactions
1597:, cyclic
1282:Phosphate
1225:anhydride
774:⟶
633:⟶
492:⟶
405:molecules
29:chemistry
2096:25203602
1823:See also
1763:to form
1761:alcohols
1659:Ammonium
1655:polarity
1575:[HPO
1451:, where
1223:) is an
1014:, where
854:hydrogen
333:pharmacy
304:for the
119:, where
87:hydrogen
51:to four
3544:
1651:soluble
1601:called
1267:protons
1221:
1206:
179:) from
173:protons
148:
133:
2158:
2094:
1793:esters
1663:alkali
1628:and a
1599:anions
1586:where
1520:[H
1487:[P
1460:[P
1434:[H
1404:[P
1378:[H
1328:, and
862:oxygen
339:, and
317:esters
280:[P
230:[H
188:anions
84:acidic
76:cycles
53:oxygen
49:bonded
2132:(PDF)
2117:(PDF)
2043:(PDF)
1816:BINOL
1773:ester
1670:salts
1647:water
413:water
385:IUPAC
347:Acids
313:salts
209:) or
3728:CmPO
3720:AmPO
3712:PuPO
3697:U(PO
3670:AcPO
3657:YbPO
3649:TmPO
3641:ErPO
3633:HoPO
3625:DyPO
3617:TbPO
3609:GdPO
3601:EuPO
3593:SmPO
3585:PmPO
3577:NdPO
3569:PrPO
3561:CePO
3553:LaPO
3465:BiPO
3426:AuPO
3397:LuPO
3347:-SbO
3340:SbPO
3329:InPO
3202:GaPO
3130:FePO
3107:MnPO
3084:CrPO
3065:ScPO
2979:AlPO
2092:PMID
2055:2010
2026:2010
1799:and
1751:The
1695:Uses
1661:and
1297:are
909:and
905:for
438:and
315:and
213:(if
194:(if
96:+2−2
31:, a
3750:No
3747:Md
3744:Fm
3741:Es
3738:Cf
3735:Bk
3708:Np
3693:Pa
3682:(PO
3666:**
3537:Og
3534:Ts
3531:Lv
3528:Mc
3525:Fl
3522:Nh
3519:Cn
3516:Rg
3513:Ds
3510:Mt
3507:Hs
3504:Bh
3501:Sg
3498:Db
3495:Rf
3492:Lr
3489:**
3486:Ra
3483:Fr
3478:Rn
3475:At
3472:Po
3453:(PO
3433:Hg
3422:Pt
3419:Ir
3416:Os
3413:Re
3407:Ta
3404:Hf
3382:(PO
3360:Xe
3354:Te
3336:Sn
3317:(PO
3297:Pd
3294:Rh
3291:Ru
3288:Tc
3285:Mo
3282:Nb
3271:(PO
3259:YPO
3245:(PO
3223:Kr
3220:Br
3216:-Se
3212:As
3209:Ge
3190:(PO
3174:(PO
3158:(PO
3142:(PO
3119:(PO
3096:(PO
3076:VPO
3072:Ti
3051:(PO
3028:HPO
3007:Ar
3004:Cl
2993:+SO
2986:Si
2967:(PO
2951:NaH
2944:HPO
2923:Ne
2889:HPO
2881:(NH
2866:(NH
2855:+BO
2848:BPO
2844:Be
2827:He
2607:PCl
2599:PCl
2591:PBr
2583:PBr
2575:PBr
2555:ZrP
2549:ZrP
2529:ZnP
2524:YbP
2514:TmP
2505:ThP
2495:SnP
2489:TbP
2468:SmP
2462:SmP
2457:ScP
2452:PuP
2443:PrP
2437:PrP
2428:PtP
2407:OsP
2387:NpP
2382:NdP
2377:NbP
2357:MoP
2351:MoP
2346:LuP
2332:LaP
2327:InP
2322:HoP
2317:HfP
2303:FeP
2298:AuP
2293:GdP
2288:EuP
2283:ErP
2278:DyP
2226:BiP
2216:AsP
2211:AlP
2082:doi
2078:114
1971:doi
1941:doi
1908:doi
1785:−OH
1769:−OH
1759:of
1753:−OH
1731:by
1723:in
1555:+ 2
1525:+2−
1318:HPO
952:or
927:HPO
888:or
276:+ 2
272:− 2
256:+1−
239:+2−
226:+ 1
222:− 2
207:+ 2
203:− 2
139:+ 2
113:+1−
27:In
3769::
3678:Th
3549:*
3449:Pb
3441:PO
3437:Tl
3410:W
3393:*
3378:Ba
3370:PO
3366:Cs
3357:I
3313:Cd
3305:PO
3301:Ag
3267:Zr
3241:Sr
3233:PO
3229:Rb
3186:Zn
3170:Cu
3154:Ni
3138:Co
3115:Fe
3092:Mn
3047:Ca
3039:PO
3035:KH
3017:PO
3000:-S
2989:P
2963:Mg
2955:PO
2940:Na
2933:PO
2929:Na
2919:+F
2915:O
2911:-N
2904:PO
2896:NH
2874:PO
2862:C
2837:PO
2833:Li
2808:PO
2747:10
2676:PO
2659:PN
2651:PH
2643:PI
2635:PF
2627:PF
2619:Cl
2537:Zn
2519:YP
2477:Sr
2417:Ru
2393:Np
2367:Mo
2337:Li
2308:Fe
2269:Cu
2257:Cd
2245:Ca
2232:Cs
2221:BP
2125:65
2123:.
2119:.
2090:.
2076:.
2072:.
2045:.
1967:38
1937:74
1935:.
1931:.
1904:62
1902:.
1898:.
1803:.
1715:,
1711:,
1632:.
1621:18
1611:Na
1559:pH
1542:+1
1493:13
1482:13
1466:10
1447:10
1436:5−
1429:10
1380:4−
1347:.
1337:PO
1321:2−
1313:,
1306:3−
1303:PO
1292:PO
1257:.
1254:10
1243:,
1212:+2
1204:=
1186:10
1134:13
1107:10
1047:PO
1011:+1
993:+2
989:−2
917:.
898:.
885:+1
871:+2
809:13
757:PO
732:10
668:10
616:PO
475:PO
432:,
374:PO
368:,
343:.
335:,
331:,
327:,
323:,
296:+1
268:=
235:−2
199:=
150:.
74:,
65:PO
3730:4
3722:4
3714:4
3703:2
3701:)
3699:4
3688:4
3686:)
3684:4
3680:3
3672:4
3659:4
3651:4
3643:4
3635:4
3627:4
3619:4
3611:4
3603:4
3595:4
3587:4
3579:4
3571:4
3563:4
3555:4
3467:4
3459:2
3457:)
3455:4
3451:3
3443:4
3439:3
3428:4
3399:4
3388:2
3386:)
3384:4
3380:3
3372:4
3368:3
3349:4
3342:4
3331:4
3323:2
3321:)
3319:4
3315:3
3307:4
3303:3
3277:4
3275:)
3273:4
3269:3
3261:4
3251:2
3249:)
3247:4
3243:3
3235:4
3231:3
3204:4
3196:2
3194:)
3192:4
3188:3
3180:2
3178:)
3176:4
3172:3
3164:2
3162:)
3160:4
3156:3
3148:2
3146:)
3144:4
3140:3
3132:4
3125:2
3123:)
3121:4
3117:3
3109:4
3102:2
3100:)
3098:4
3094:3
3086:4
3078:4
3067:4
3057:2
3055:)
3053:4
3049:3
3041:4
3037:2
3030:4
3026:2
3024:K
3019:4
3015:3
3013:K
2995:4
2981:4
2973:2
2971:)
2969:4
2965:3
2957:4
2953:2
2946:4
2942:2
2935:4
2931:3
2906:4
2902:2
2900:H
2898:4
2891:4
2887:2
2885:)
2883:4
2876:4
2872:3
2870:)
2868:4
2857:3
2850:4
2839:4
2835:3
2810:4
2806:3
2804:H
2782:e
2775:t
2768:v
2745:S
2743:4
2741:P
2735:x
2733:S
2731:4
2729:P
2723:3
2721:S
2719:4
2717:P
2711:5
2709:O
2707:2
2705:P
2699:4
2697:O
2695:2
2693:P
2687:3
2685:O
2683:2
2681:P
2670:5
2668:N
2666:3
2664:P
2653:3
2645:3
2637:5
2629:3
2621:4
2617:2
2615:P
2609:5
2601:3
2593:7
2585:5
2577:3
2557:2
2543:2
2541:P
2539:3
2531:2
2507:7
2497:3
2483:2
2481:P
2479:3
2470:5
2445:5
2430:2
2421:P
2419:2
2409:2
2399:4
2397:P
2395:3
2371:P
2369:3
2359:2
2341:P
2339:3
2312:P
2310:3
2273:P
2271:3
2263:2
2261:P
2259:3
2251:2
2249:P
2247:3
2238:5
2236:P
2234:2
2187:e
2180:t
2173:v
2098:.
2084::
2057:.
2028:.
1977:.
1973::
1949:.
1943::
1916:.
1910::
1818:.
1789:H
1777:R
1649:-
1619:O
1617:6
1615:P
1613:6
1609:(
1595:H
1588:x
1582:x
1579:]
1577:3
1553:n
1548:k
1544:]
1540:n
1538:3
1536:O
1533:n
1530:P
1527:k
1523:n
1513:]
1511:3
1509:)
1507:3
1495:]
1491:O
1489:4
1480:O
1478:4
1476:P
1474:6
1472:H
1468:]
1464:O
1462:3
1453:k
1449:]
1445:O
1443:3
1441:P
1438:k
1427:O
1425:3
1423:P
1421:5
1419:H
1412:]
1410:7
1408:O
1406:2
1397:k
1393:]
1391:7
1389:O
1387:2
1385:P
1382:k
1373:7
1371:O
1369:2
1367:P
1365:4
1363:H
1343:4
1340:−
1335:2
1333:H
1324:4
1309:4
1294:4
1290:3
1288:H
1270:H
1252:O
1250:4
1248:P
1239:n
1237:5
1235:O
1232:n
1230:2
1228:P
1218:2
1215:/
1210:n
1202:x
1184:O
1182:4
1180:P
1161:9
1159:O
1157:3
1155:P
1153:3
1151:H
1132:O
1130:4
1128:P
1126:6
1124:H
1105:O
1103:3
1101:P
1099:5
1097:H
1078:7
1076:O
1074:2
1072:P
1070:4
1068:H
1049:4
1045:3
1043:H
1020:x
1016:n
1009:x
1007:−
1005:n
1003:3
1001:O
998:n
995:P
991:x
987:n
984:H
977:O
975:2
973:H
968:9
966:O
964:3
962:P
960:3
958:H
929:3
896:H
893:n
883:n
881:3
879:O
876:n
873:P
869:n
866:H
833:O
825:2
821:H
817:+
805:O
796:4
792:P
783:6
779:H
761:4
748:3
744:H
740:+
728:O
719:3
715:P
706:5
702:H
692:O
684:2
680:H
676:+
664:O
655:3
651:P
642:5
638:H
620:4
607:3
603:H
599:+
591:7
587:O
578:2
574:P
565:4
561:H
551:O
543:2
539:H
535:+
527:7
523:O
514:2
510:P
501:4
497:H
479:4
466:3
462:H
457:2
376:4
372:3
370:H
298:]
294:x
292:−
290:n
288:3
286:O
283:n
274:x
270:n
266:k
261:]
258:x
254:n
252:3
250:O
247:n
244:P
241:k
237:x
233:n
224:x
220:n
215:k
205:x
201:n
197:k
181:k
177:H
175:(
145:2
142:/
137:n
125:x
121:n
115:x
111:n
109:3
107:O
104:n
101:P
98:x
94:n
91:H
67:4
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