GB675779A - A process for the manufacture of substituted phosphorus oxyacids - Google Patents
A process for the manufacture of substituted phosphorus oxyacidsInfo
- Publication number
- GB675779A GB675779A GB3155849A GB3155849A GB675779A GB 675779 A GB675779 A GB 675779A GB 3155849 A GB3155849 A GB 3155849A GB 3155849 A GB3155849 A GB 3155849A GB 675779 A GB675779 A GB 675779A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salt
- phosphoric acid
- phosphate
- nitrobenzyl
- dibenzyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003017 phosphorus Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 6
- 150000003946 cyclohexylamines Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 4
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 3
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 150000005691 triesters Chemical class 0.000 abstract 3
- PBBGSZCBWVPOOL-HDICACEKSA-N 4-[(1r,2s)-1-ethyl-2-(4-hydroxyphenyl)butyl]phenol Chemical compound C1([C@H](CC)[C@H](CC)C=2C=CC(O)=CC=2)=CC=C(O)C=C1 PBBGSZCBWVPOOL-HDICACEKSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- JSPSCIMSQMTXFU-UHFFFAOYSA-N bis[(4-nitrophenyl)methyl] hydrogen phosphate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COP(=O)(O)OCC1=CC=C([N+]([O-])=O)C=C1 JSPSCIMSQMTXFU-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- NSBNXCZCLRBQTA-UHFFFAOYSA-N dibenzyl bis(phenylmethoxy)phosphoryl phosphate Chemical compound C=1C=CC=CC=1COP(OP(=O)(OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)(=O)OCC1=CC=CC=C1 NSBNXCZCLRBQTA-UHFFFAOYSA-N 0.000 abstract 2
- 239000001177 diphosphate Substances 0.000 abstract 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 abstract 2
- 235000011180 diphosphates Nutrition 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 229950001996 hexestrol Drugs 0.000 abstract 2
- 150000001457 metallic cations Chemical class 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- OJNRZXCXPGBBSQ-UHFFFAOYSA-N (2-benzylphenyl) dihydrogen phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1CC1=CC=CC=C1 OJNRZXCXPGBBSQ-UHFFFAOYSA-N 0.000 abstract 1
- NUMYTLIHYKESKM-UHFFFAOYSA-N (4-nitrophenyl)methyl thiocyanate Chemical compound [O-][N+](=O)C1=CC=C(CSC#N)C=C1 NUMYTLIHYKESKM-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- 229940093475 2-ethoxyethanol Drugs 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- OPOVFSUJUFEFKK-UHFFFAOYSA-N BrC1CC(C(CC1)(OP(O)(O)=O)CC1=CC=CC=C1)O Chemical compound BrC1CC(C(CC1)(OP(O)(O)=O)CC1=CC=CC=C1)O OPOVFSUJUFEFKK-UHFFFAOYSA-N 0.000 abstract 1
- HAQOZLTYKLQPCC-UHFFFAOYSA-N C(C1=CC=CC=C1)C1(C(CCCC1)O)OP(O)(O)=O Chemical compound C(C1=CC=CC=C1)C1(C(CCCC1)O)OP(O)(O)=O HAQOZLTYKLQPCC-UHFFFAOYSA-N 0.000 abstract 1
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 abstract 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical class C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 abstract 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 241001180649 Myrcia group Species 0.000 abstract 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 abstract 1
- JUIUXBHZFNHITF-IEOSBIPESA-N [(2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] dihydrogen phosphate Chemical compound OP(=O)(O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C JUIUXBHZFNHITF-IEOSBIPESA-N 0.000 abstract 1
- NWJXKHVJFGAOMY-DYKIIFRCSA-N [(8r,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] dihydrogen phosphate Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)OP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 NWJXKHVJFGAOMY-DYKIIFRCSA-N 0.000 abstract 1
- BTTFROAXTOXGLB-UHFFFAOYSA-N [N+](=O)([O-])C1CC(C(CC1)(OP(O)(O)=O)CC1=CC=CC=C1)O Chemical compound [N+](=O)([O-])C1CC(C(CC1)(OP(O)(O)=O)CC1=CC=CC=C1)O BTTFROAXTOXGLB-UHFFFAOYSA-N 0.000 abstract 1
- GRGVCAFATGPUAB-UHFFFAOYSA-N [S-]C#N.C[NH+]1CCOCC1 Chemical class [S-]C#N.C[NH+]1CCOCC1 GRGVCAFATGPUAB-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 159000000009 barium salts Chemical class 0.000 abstract 1
- KLBUYXMPOOLBJE-UHFFFAOYSA-L barium(2+);diethyl phosphate Chemical compound [Ba+2].CCOP([O-])(=O)OCC.CCOP([O-])(=O)OCC KLBUYXMPOOLBJE-UHFFFAOYSA-L 0.000 abstract 1
- YTFJQDNGSQJFNA-UHFFFAOYSA-N benzyl dihydrogen phosphate Chemical compound OP(O)(=O)OCC1=CC=CC=C1 YTFJQDNGSQJFNA-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000003939 benzylamines Chemical class 0.000 abstract 1
- IHHYYBHWNAIJPZ-UHFFFAOYSA-N benzylazanium;thiocyanate Chemical compound [S-]C#N.[NH3+]CC1=CC=CC=C1 IHHYYBHWNAIJPZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- VKGHLDSEBVEAME-UHFFFAOYSA-N cyclohexanamine;thiocyanic acid Chemical compound SC#N.NC1CCCCC1 VKGHLDSEBVEAME-UHFFFAOYSA-N 0.000 abstract 1
- FUDFVXRUESNVBI-UHFFFAOYSA-N dibenzyl phenyl phosphate Chemical compound C=1C=CC=CC=1COP(OC=1C=CC=CC=1)(=O)OCC1=CC=CC=C1 FUDFVXRUESNVBI-UHFFFAOYSA-N 0.000 abstract 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-M dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-M 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract 1
- 238000010494 dissociation reaction Methods 0.000 abstract 1
- 230000005593 dissociations Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical class CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910003002 lithium salt Inorganic materials 0.000 abstract 1
- 159000000002 lithium salts Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- VSNJIJJTZGHSMT-UHFFFAOYSA-N morpholin-4-ium;thiocyanate Chemical compound [S-]C#N.C1COCC[NH2+]1 VSNJIJJTZGHSMT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 150000002780 morpholines Chemical class 0.000 abstract 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- -1 orthophosphoric acid triesters Chemical class 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000003053 piperidines Chemical class 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 abstract 1
- 229940116357 potassium thiocyanate Drugs 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003567 thiocyanates Chemical class 0.000 abstract 1
- VFVYCNYEQFSMLG-UHFFFAOYSA-N tris[(4-nitrophenyl)methyl] phosphate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COP(=O)(OCC=1C=CC(=CC=1)[N+]([O-])=O)OCC1=CC=C([N+]([O-])=O)C=C1 VFVYCNYEQFSMLG-UHFFFAOYSA-N 0.000 abstract 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
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)
Abstract
A process for the partial de-esterification of organic orthophosphoric tri-esters of the general formula <FORM:0675779/IV (b)/1> in which X is an organic residue derived from the organic compound X.OH, where OH is a phenolic or alcoholic hydroxy group, R3 and R4 are the same or different and each is an alkyl or aromatic group, to produce the corresponding di-esters, wherein the tri-ester is treated in a polar or substantially polar solvent with a salt of the general formula [R.S-]vM, wherein R is -CN, CS.O Alkyl or -CS.NR3R2 (where R1 and R2 each represent hydrogen or an alkyl or aralkyl group or together with the N atom to which they are attached, form a piperidino or morpholino group) or any carbon containing group which renders the compound RSH acidic, M is a metallic cation, preferably of the alkali metal or alkaline earth series or a non-metallic cation such as ammonium or substituted ammonium derived from strong amines, and v is the valency of the cation M. Groups which may be removed include straight or branched chain alkyl groups and phenylmethyl, naphthylmethyl, pyridylmethyl, quinolylmethyl or pyrimidylmethyl groups. The solvents are neutral or substantially neutral solvents capable of ionizing the reagents used in the partial de-esterification. The carbon-containing group which renders the compound RSH acidic is one yielding a mercaptol capable of forming a stable salt with the cation M. "Strong amines" are those having a dissociation constant greater than 1 X 10-7, e.g. cyclohexylamine, benzylamine, morpholine, b -phenyl-ethylamine and piperidine. Thiocyanates are the preferred de-esterifying reagents. Where the groups R3 and R4 are different, aromatically-substituted groups are removed preferentially to alkyl groups. A mixture of products may result when R3 and R4 are different aromatic groups. In examples, di-(p-nitrobenzyl) phosphoric acid is prepared by reacting tri-(p-nitrobenzyl) phosphate with (1) potassium thiocyanate; (2) ammonium thiocyanate; (3) potassium ethyl xanthate, and as its morpholine, cyclohexyl amine benzylamine and piperidine salts from the tri-ester; and (4) morpholinium thiocyanate; (5) cyclohexyl ammonium thiocyanate; (6) benzyl-ammonium thiocyanate; and (16) piperidinium-N-piperidinodithioformate. In an analagous manner are prepared: (7) the cyclohexylamine salt of and (10) the benzylamine salt of benzyl 2-hydroxycyclohexyl phosphoric acid; (8) the cyclohexylamine salt of p-bromobenzyl 2-hydroxycyclohexyl phosphoric acid; (9) the cyclohexylamine salt of p-nitrobenzyl 2-hydroxy-cyclohexyl phosphoric acid; (11) sym.-di-potassium dibenzyl hexoestrol diphosphate (from hexoestrol diphosphate tetrabenzyl ester); (12) sym.-di-potassium dibenzyl stilboestrol diphosphate and (13) the barium salt (from stilboestrol diphosphate tetrabenzyl ester); (14) sym.-di-cyclohexylamine salt of dibenzyl stilboestrol diphosphoric acid; (15) barium diethyl phosphate; (17) 4-methyl-morpholine salt of di-(p-nitrobenzyl) phosphoric acid; (18), (19) and (20) the cyclohexyl amine, benzylamine and lithium salts of dibenzyl phosphoric acid; (21) the cyclohexylamine salt of benzyl phenyl phosphoric acid (from dibenzyl phenyl phosphate); (22), (23), (24) the cyclohexylamine salt of diphenyl phosphoric acid (from diphenyl, ethyl, propyl, or isopropyl phosphates; (25) morpholine salt of diphenyl phosphoric acid; (26) the cyclohexylamine salt of b -(2 : 3 : 4 : 6-tetra-acetyl-D-glycosyl) benzyl phosphoric acid (from the corresponding dibenzyl phosphate). In (1) and (2) the by-products p-nitrobenzyl thiocyanate, and in (3) S-p-nitrobenzyl ethyl xanthate are isolated from the reaction mixture. Reagents employed include lithium and 4-methyl morpholinium thiocyanates. Other solvents mentioned are 2-ethoxyethanol, methyl ethyl ketone and n-propanol. The process may also be applied to orthophosphoric acid triesters derived from glucose-6-phosphate, vitamin E phosphate, 2-methyl-naphthohydroquinone phosphate, oestrone-3-phosphate and testosterone-17-phosphate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3155849A GB675779A (en) | 1949-12-08 | 1949-12-08 | A process for the manufacture of substituted phosphorus oxyacids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3155849A GB675779A (en) | 1949-12-08 | 1949-12-08 | A process for the manufacture of substituted phosphorus oxyacids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB675779A true GB675779A (en) | 1952-07-16 |
Family
ID=10324917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3155849A Expired GB675779A (en) | 1949-12-08 | 1949-12-08 | A process for the manufacture of substituted phosphorus oxyacids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB675779A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012011519A1 (en) * | 2010-07-22 | 2012-01-26 | 丸菱油化工業株式会社 | Fire retarding agent containing cyclic amine salt, and fire-retardant resin composition |
-
1949
- 1949-12-08 GB GB3155849A patent/GB675779A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012011519A1 (en) * | 2010-07-22 | 2012-01-26 | 丸菱油化工業株式会社 | Fire retarding agent containing cyclic amine salt, and fire-retardant resin composition |
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