1180:
1162:
1202:
1140:
999:
27:
243:
1220:
1063:
With excess water, the hydrolysis can be considered pseudo-first order. The half-life for this decomposition is dependent on the pH and temperature, being about 31 hours at 35 °C and 2.5 hours at 61 °C. A solution in acetonitrile also slowly degrades, losing 30% of active oxygen after 26 days of
944:
One method of preparation is the hydrolysis of potassium of lithium peroxydiphosphate in a strong acid such as perchloric acid. The peroxydiphosphate salts can be obtained by electrolysis of their respective phosphate salts.
874:
603:
728:
1516:
Ogata, Yoshiro; Sawaki, Yasuhiko; Ohno, Takashi (1982). "Mechanism for
Oxidation of Phenylacetylenes with Peroxymonophosphoric acid. Oxirene as an Intermediate Inconvertible to Ketocarbene".
1014:
Peroxymonophosphoric acid is a colorless, viscous liquid. It is stabilized by an intramolecular hydrogen bond. The compound is a triprotic acid with acid dissociation constants pK
1573:
Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki (1978). "Kinetics of the Baeyer-Villiger
Reaction of Acetophenones with Permonophosphoric Acid".
1384:
1424:
1132:
yield no isolable epoxides. In the cases of styrene and α-methylstyrene, acid-catalyzed alkyl migrations lead instead to the main products
899:
Peroxyphosphoric acid is usually produced by treating phosphorus pentoxide and concentrated hydrogen peroxide within an inert solvent like
289:
1460:
Battaglia, Charles J.; Edwards, John O. (1965). "The
Dissociation Constants and the Kinetics of Hydrolysis of Peroxymonophosphoric Acid".
1644:
1194:
can be converted to the corresponding phenyl acetates at 30 °C in high yields. The rate is about 100 times higher in comparison to using
1601:
Ogata, Yoshiro; Tomizawa, Kohtaro; Morikawa, Takashi (1979). "Kinetics of the
Peroxymonophosphoric Acid Oxidation of Aromatic Amines".
456:
Peroxyphosphoric acids were first synthesized and characterized in 1910 by Julius
Schmidlin and Paul Massini via the reaction between
1544:
Ogata, Yoshiro; Sawaki, Yasuhiko; Tomizawa, Kohtaro; Ohno, Takashi (1981). "Aromatic
Hydroxylation with Peroxymonophosphoric Acid".
464:. However, this reaction proceeds very vigorously and is difficult to control. Aside from phosphorus pentoxide, syntheses from
734:
478:
1488:
Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki (1979). "Oxidation of trans-Stilbene with
Peroxymonophosphoric Acid".
1382:
Harald, Jakob; Leininger, Stefan; Lehmann, Thomas; Jacobi, Sylvia; Gutewort, Sven (2007). "Peroxo
Compounds, Inorganic".
1313:
Jakob, Harald; Leininger, Stefan; Lehmann, Thomas; Jacobi, Sylvia; Gutewort, Sven (2007). "Peroxo
Compounds, Inorganic".
609:
1330:
1441:
1401:
257:
1112:. Due to the strongly acidic nature, only relatively acid-stable epoxides can be prepared from alkenes, for example
1349:
Zhu, Tian; Chang, Hou-Min; Kadia, John F. (2003). "A New Method for the
Preparation of Peroxymonophosphoric Acid".
395:
1096:
They have been examined in the context of organic synthesis, as an electrophilic reagent for the oxidation of
1168:
Peroxymonophosphoric acid is an effective reagent for the hydroxylation of aromatic rings. The conversion of
429:. It is a colorless viscous oil. Its salts are called peroxymonophosphates. Another peroxyphosphoric acid is
49:
1634:
164:
221:
124:
1065:
1026:= 12.8. In aqueous solutions it slowly undergoes hydrolysis to hydrogen peroxide and phosphoric acid.
1187:
238:
430:
376:
1639:
1256:
1546:
184:
39:
904:
879:
A less vigorous method of preparing peroxyphosphoric acid by introducing the inert solvent
457:
100:
242:
8:
1231:
1129:
1069:
469:
465:
90:
998:
144:
26:
1282:
Toennies, Gerrit (1937). "A New Method for the Preparation of Permonophosphoric Acid".
1201:
1195:
1179:
1161:
1139:
1105:
1559:
1518:
1437:
1397:
1326:
1284:
1147:
1133:
461:
883:
was described by Gerrit Toennies in 1937. This method was shown to be unsuitable in
209:
1611:
1583:
1555:
1526:
1498:
1470:
1429:
1389:
1359:
1318:
1292:
1264:
312:
1393:
1322:
1227:
1209:
983:
888:
380:
389:
1433:
1268:
1628:
1603:
1575:
1490:
1351:
884:
1462:
1191:
900:
880:
355:
1213:
1121:
1615:
1587:
1530:
1502:
1474:
1296:
1219:
1422:
Rao, A. Somasekar; Mohan, H. Rama (2001). "Monoperoxyphosphoric Acid".
1169:
426:
349:
331:
175:
1088:
Peroxyphosphoric acids and peroxyphosphates have few commercial uses.
1363:
1251:
388:
Except where otherwise noted, data are given for materials in their
987:
1072:
to give the hygroscopic potassium dihydrogenperoxymonophosphate KH
123:
1186:
The compound can be used as an effective oxidizing agent for the
1173:
1155:
1125:
1101:
1097:
422:
359:
196:
1151:
1109:
155:
1120:-stilbene. Less stable epoxides are cleaved or react further;
1176:
can be achieved at room temperature in less than four hours.
135:
113:
1381:
1064:
storage at 5 °C. Relatively stable salts can be obtained by
226:
1312:
869:{\displaystyle {\ce {H4P2O7 + H2O2 -> H3PO5 + H3PO4}}}
862:
849:
833:
820:
804:
791:
775:
762:
749:
716:
703:
683:
670:
650:
637:
624:
591:
578:
555:
539:
526:
506:
493:
1543:
598:{\displaystyle {\ce {P2O5 + 2H2O2 + H2O -> 2H3PO5}}}
1600:
737:
612:
481:
723:{\displaystyle {\ce {H4P4O12 + 4H2O2 -> 4H3PO5}}}
1091:
1572:
1487:
868:
722:
597:
1626:
1459:
1249:
208:
1515:
99:
1425:Encyclopedia of Reagents for Organic Synthesis
1385:Ullmann's Encyclopedia of Industrial Chemistry
1315:Ullmann's Encyclopedia of Industrial Chemistry
1348:
1010:, displaying the intramolecular hydrogen bond
1252:"PhosphormonopersĂ€ure und ĂberphosphorsĂ€ure"
1218:
1200:
1178:
1160:
1138:
460:and highly-concentrated aqueous solution of
1136:and 2-phenylpropionic acid, respectively.
276:InChI=1S/H3O5P/c1-5-6(2,3)4/h1H,(H2,2,3,4)
266:InChI=1S/H3O5P/c1-5-6(2,3)4/h1H,(H2,2,3,4)
241:
183:
1308:
1306:
1250:Schmidlin, Julius; Massini, Paul (1910).
982:Peroxydiphosphoric acid is obtained when
692:
659:
567:
515:
1421:
1281:
997:
1275:
894:
237:
54:(dioxidanido)dihydroxidooxidophosphorus
1627:
1388:. WileyâVCH Verlag. pp. 310â311.
1303:
1230:with peroxymonophosphoric acid gives
1083:
269:Key: MPNNOLHYOHFJKL-UHFFFAOYSA-N
163:
143:
1455:
1453:
1417:
1415:
1413:
1377:
1375:
1373:
1344:
1342:
199:
13:
1645:Substances discovered in the 1910s
1212:are oxidized to the corresponding
14:
1656:
1450:
1410:
1370:
1339:
1092:Reactions with organic compounds
25:
1594:
1566:
1537:
392:(at 25 °C , 100 kPa).
1509:
1481:
1243:
1208:Tertiary aromatic amines like
990:or oxidized electrolytically.
807:
686:
561:
451:
1:
1560:10.1016/S0040-4020(01)92087-3
1394:10.1002/14356007.a19_177.pub2
1323:10.1002/14356007.a19_177.pub2
1237:
1068:with bases, for example with
993:
7:
1150:at room temperature yields
10:
1661:
336:114.00 g/mol
20:Peroxymonophosphoric acid
1434:10.1002/047084289X.rm287m
1428:. John Wiley & Sons.
1269:10.1002/cber.191004301195
1188:Baeyer-Villiger oxidation
408:Peroxymonophosphoric acid
386:
365:
305:
285:
253:
83:
72:peroxomonophosphoric acid
66:monoperoxyphosphoric acid
60:
48:
38:
33:
24:
1154:, presumably through an
431:peroxydiphosphoric acid
377:peroxydiphosphoric acid
1257:Ber. Dtsch. Chem. Ges.
1223:
1205:
1183:
1165:
1143:
1011:
870:
724:
599:
69:permonophosphoric acid
1222:
1204:
1182:
1164:
1142:
1116:-stilbene oxide from
1001:
871:
725:
600:
50:Systematic IUPAC name
43:peroxyphosphoric acid
16:Oxyacid of phosphorus
905:carbon tetrachloride
895:Contemporary methods
735:
610:
479:
472:were also reported.
458:phosphorus pentoxide
1635:Phosphorus oxoacids
1616:10.1021/jo01317a009
1588:10.1021/jo00406a025
1531:10.1021/ja00365a039
1503:10.1021/jo01328a006
1475:10.1021/ic50026a024
1297:10.1021/ja01282a037
1070:potassium hydroxide
864:
851:
835:
822:
806:
793:
777:
764:
751:
718:
705:
685:
672:
652:
639:
626:
593:
580:
557:
541:
528:
508:
495:
466:metaphosphoric acid
21:
1224:
1206:
1196:peroxybenzoic acid
1184:
1166:
1144:
1106:aromatic compounds
1084:Uses and reactions
1012:
1002:The structure of H
866:
852:
839:
823:
810:
794:
781:
765:
752:
739:
720:
706:
693:
673:
660:
640:
627:
614:
595:
581:
568:
545:
529:
516:
496:
483:
396:Infobox references
366:Related compounds
19:
1582:(12): 2417â2419.
1519:J. Am. Chem. Soc.
1497:(14): 2362â2364.
1285:J. Am. Chem. Soc.
1148:diphenylacetylene
1146:The oxidation of
1134:phenylacetic acid
855:
842:
826:
813:
797:
784:
768:
755:
742:
709:
696:
676:
663:
643:
630:
617:
584:
571:
560:
548:
532:
519:
499:
486:
470:diphosphoric acid
462:hydrogen peroxide
404:Chemical compound
402:
401:
372:Related compounds
222:CompTox Dashboard
125:Interactive image
1652:
1620:
1619:
1598:
1592:
1591:
1570:
1564:
1563:
1554:(8): 1485â1486.
1541:
1535:
1534:
1513:
1507:
1506:
1485:
1479:
1478:
1457:
1448:
1447:
1419:
1408:
1407:
1379:
1368:
1367:
1346:
1337:
1336:
1310:
1301:
1300:
1279:
1273:
1272:
1263:(1): 1162â1171.
1247:
1059:
986:is treated with
978:
962:O + 4 H â H
940:
875:
873:
872:
867:
865:
863:
860:
853:
850:
847:
840:
834:
831:
824:
821:
818:
811:
805:
802:
795:
792:
789:
782:
776:
773:
766:
763:
760:
753:
750:
747:
740:
729:
727:
726:
721:
719:
717:
714:
707:
704:
701:
694:
684:
681:
674:
671:
668:
661:
651:
648:
641:
638:
635:
628:
625:
622:
615:
604:
602:
601:
596:
594:
592:
589:
582:
579:
576:
569:
558:
556:
553:
546:
540:
537:
530:
527:
524:
517:
507:
504:
497:
494:
491:
484:
447:
420:
313:Chemical formula
246:
245:
230:
228:
212:
201:
187:
167:
147:
127:
103:
29:
22:
18:
1660:
1659:
1655:
1654:
1653:
1651:
1650:
1649:
1625:
1624:
1623:
1599:
1595:
1571:
1567:
1542:
1538:
1514:
1510:
1486:
1482:
1458:
1451:
1444:
1420:
1411:
1404:
1380:
1371:
1364:10.1139/v03-010
1347:
1340:
1333:
1311:
1304:
1280:
1276:
1248:
1244:
1240:
1232:Îł-butyrolactone
1210:dimethylaniline
1130:α-methylstyrene
1094:
1086:
1079:
1075:
1058:
1054:
1050:
1046:
1042:
1038:
1034:
1030:
1025:
1021:
1017:
1009:
1005:
996:
984:phosphoric acid
977:
973:
969:
965:
961:
957:
953:
949:
939:
935:
931:
927:
923:
919:
915:
911:
897:
889:isoamyl alcohol
861:
856:
848:
843:
832:
827:
819:
814:
803:
798:
790:
785:
774:
769:
761:
756:
748:
743:
738:
736:
733:
732:
715:
710:
702:
697:
682:
677:
669:
664:
649:
644:
636:
631:
623:
618:
613:
611:
608:
607:
590:
585:
577:
572:
554:
549:
538:
533:
525:
520:
505:
500:
492:
487:
482:
480:
477:
476:
454:
446:
442:
438:
434:
419:
415:
411:
405:
398:
393:
381:phosphoric acid
373:
325:
321:
315:
301:
298:
293:
292:
281:
278:
277:
271:
270:
267:
261:
260:
249:
231:
224:
215:
202:
190:
170:
150:
130:
117:
106:
93:
79:
78:
56:
55:
44:
17:
12:
11:
5:
1658:
1648:
1647:
1642:
1637:
1622:
1621:
1610:(3): 352â355.
1593:
1565:
1536:
1525:(1): 216â219.
1508:
1480:
1469:(4): 552â558.
1449:
1442:
1409:
1402:
1369:
1358:(2): 156â160.
1338:
1332:978-3527306732
1331:
1302:
1291:(3): 555â557.
1274:
1241:
1239:
1236:
1190:. Substituted
1158:intermediate.
1093:
1090:
1085:
1082:
1077:
1073:
1066:neutralization
1061:
1060:
1056:
1052:
1048:
1044:
1040:
1036:
1032:
1023:
1019:
1015:
1007:
1003:
995:
992:
980:
979:
975:
971:
967:
963:
959:
955:
951:
942:
941:
937:
933:
929:
925:
921:
917:
913:
896:
893:
877:
876:
859:
846:
838:
830:
817:
809:
801:
788:
780:
772:
759:
746:
730:
713:
700:
691:
688:
680:
667:
658:
655:
647:
634:
621:
605:
588:
575:
566:
563:
552:
544:
536:
523:
514:
511:
503:
490:
453:
450:
444:
440:
436:
417:
413:
403:
400:
399:
394:
390:standard state
387:
384:
383:
374:
371:
368:
367:
363:
362:
352:
346:
345:
344:colorless oil
342:
338:
337:
334:
328:
327:
323:
319:
316:
311:
308:
307:
303:
302:
300:
299:
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282:
280:
279:
275:
274:
272:
268:
265:
264:
256:
255:
254:
251:
250:
248:
247:
239:DTXSID70422533
234:
232:
220:
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216:
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205:
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195:
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191:
189:
188:
180:
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96:
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89:
86:
85:
81:
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73:
70:
67:
63:
62:
58:
57:
53:
52:
46:
45:
42:
36:
35:
31:
30:
15:
9:
6:
4:
3:
2:
1657:
1646:
1643:
1641:
1640:Mineral acids
1638:
1636:
1633:
1632:
1630:
1617:
1613:
1609:
1606:
1605:
1604:J. Org. Chem.
1597:
1589:
1585:
1581:
1578:
1577:
1576:J. Org. Chem.
1569:
1561:
1557:
1553:
1549:
1548:
1540:
1532:
1528:
1524:
1521:
1520:
1512:
1504:
1500:
1496:
1493:
1492:
1491:J. Org. Chem.
1484:
1476:
1472:
1468:
1465:
1464:
1456:
1454:
1445:
1443:9780470842898
1439:
1435:
1431:
1427:
1426:
1418:
1416:
1414:
1405:
1403:9783527306732
1399:
1395:
1391:
1387:
1386:
1378:
1376:
1374:
1365:
1361:
1357:
1354:
1353:
1352:Can. J. Chem.
1345:
1343:
1334:
1328:
1324:
1320:
1316:
1309:
1307:
1298:
1294:
1290:
1287:
1286:
1278:
1270:
1266:
1262:
1259:
1258:
1253:
1246:
1242:
1235:
1233:
1229:
1226:Oxidation of
1221:
1217:
1215:
1211:
1203:
1199:
1197:
1193:
1192:acetophenones
1189:
1181:
1177:
1175:
1171:
1163:
1159:
1157:
1153:
1149:
1141:
1137:
1135:
1131:
1127:
1123:
1119:
1115:
1111:
1107:
1103:
1099:
1089:
1081:
1071:
1067:
1029:
1028:
1027:
1000:
991:
989:
985:
948:
947:
946:
910:
909:
908:
906:
902:
892:
890:
886:
885:diethyl ether
882:
857:
844:
836:
828:
815:
799:
786:
778:
770:
757:
744:
731:
711:
698:
689:
678:
665:
656:
653:
645:
632:
619:
606:
586:
573:
564:
550:
542:
534:
521:
512:
509:
501:
488:
475:
474:
473:
471:
467:
463:
459:
449:
432:
428:
424:
409:
397:
391:
385:
382:
378:
375:
370:
369:
364:
361:
357:
353:
351:
348:
347:
343:
340:
339:
335:
333:
330:
329:
317:
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310:
309:
304:
295:
294:
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284:
273:
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244:
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236:
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233:
223:
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218:
211:
207:
206:
204:
198:
194:
193:
186:
182:
181:
179:
177:
174:
173:
166:
165:ChEMBL1162310
162:
161:
159:
157:
154:
153:
146:
142:
141:
139:
137:
134:
133:
126:
122:
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119:
115:
110:
109:
102:
98:
97:
95:
92:
88:
87:
82:
74:
71:
68:
65:
64:
59:
51:
47:
41:
37:
32:
28:
23:
1607:
1602:
1596:
1579:
1574:
1568:
1551:
1545:
1539:
1522:
1517:
1511:
1494:
1489:
1483:
1466:
1463:Inorg. Chem.
1461:
1423:
1383:
1355:
1350:
1314:
1288:
1283:
1277:
1260:
1255:
1245:
1225:
1207:
1185:
1167:
1145:
1117:
1113:
1095:
1087:
1062:
1022:= 5.5 and pK
1013:
981:
943:
901:acetonitrile
898:
881:acetonitrile
878:
455:
407:
406:
356:acetonitrile
84:Identifiers
61:Other names
1547:Tetrahedron
1214:amine oxide
1122:cyclohexene
452:Preparation
354:soluble in
341:Appearance
306:Properties
297:OOP(=O)(O)O
145:CHEBI:29282
1629:Categories
1238:References
1170:mesitylene
994:Properties
427:phosphorus
350:Solubility
332:Molar mass
176:ChemSpider
112:3D model (
101:13598-52-2
91:CAS Number
40:IUPAC name
1018:= 1.1, pK
808:⟶
687:⟶
562:⟶
988:fluorine
932:O â 4H
421:) is an
1174:mesitol
1156:oxirene
1126:styrene
1102:alkynes
1098:alkenes
1043:O â H
423:oxyacid
360:dioxane
326:
210:6326786
197:PubChem
185:4885506
1440:
1400:
1329:
1152:benzil
1128:, and
1110:amines
290:SMILES
156:ChEMBL
34:Names
1118:trans
1114:trans
958:) + H
258:InChI
136:ChEBI
114:JSmol
1438:ISBN
1398:ISBN
1327:ISBN
1108:and
928:+ 2H
920:+ 4H
468:and
75:PMPA
1612:doi
1584:doi
1556:doi
1527:doi
1523:104
1499:doi
1471:doi
1430:doi
1390:doi
1360:doi
1319:doi
1293:doi
1265:doi
1228:THF
1172:to
1051:+ H
1039:+ H
970:+ H
903:or
887:or
425:of
227:EPA
200:CID
1631::
1608:44
1580:43
1552:37
1550:.
1495:44
1452:^
1436:.
1412:^
1396:.
1372:^
1356:81
1341:^
1325:.
1317:.
1305:^
1289:59
1261:43
1254:.
1234:.
1216:.
1198:.
1124:,
1104:,
1100:,
1080:.
1076:PO
1047:PO
1035:PO
1024:a3
1020:a2
1016:a1
1006:PO
974:PO
966:PO
950:(P
936:PO
918:10
907:.
891:.
854:PO
825:PO
708:PO
646:12
583:PO
448:.
433:,
416:PO
379:;
358:,
322:PO
1618:.
1614::
1590:.
1586::
1562:.
1558::
1533:.
1529::
1505:.
1501::
1477:.
1473::
1467:4
1446:.
1432::
1406:.
1392::
1366:.
1362::
1335:.
1321::
1299:.
1295::
1271:.
1267::
1078:5
1074:2
1057:2
1055:O
1053:2
1049:4
1045:3
1041:2
1037:5
1033:3
1031:H
1008:5
1004:3
976:4
972:3
968:5
964:3
960:2
956:8
954:O
952:2
938:5
934:3
930:2
926:2
924:O
922:2
916:O
914:4
912:P
858:4
845:3
841:H
837:+
829:5
816:3
812:H
800:2
796:O
787:2
783:H
779:+
771:7
767:O
758:2
754:P
745:4
741:H
712:5
699:3
695:H
690:4
679:2
675:O
666:2
662:H
657:4
654:+
642:O
633:4
629:P
620:4
616:H
587:5
574:3
570:H
565:2
559:O
551:2
547:H
543:+
535:2
531:O
522:2
518:H
513:2
510:+
502:5
498:O
489:2
485:P
445:8
443:O
441:2
439:P
437:4
435:H
418:5
414:3
412:H
410:(
324:5
320:3
318:H
229:)
225:(
116:)
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