CA1052377A - Procede pour la preparation de phosphorothioates et de phenylphosphonothioates - Google Patents

Procede pour la preparation de phosphorothioates et de phenylphosphonothioates

Info

Publication number: CA1052377A
Authority: CA; Canada
Prior art keywords: alkyl; chloride; carbon atoms; formula; nitro
Prior art date: 1975-08-05
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

Application number

CA232,871A

Other languages

English (en)

Other versions

CA232871S (en

Inventor

Masao Yoshimine

Stanley D. Mcgregor

Harold H. Freedman

Lorraine M. Kroposki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

Priority date (The priority date 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 date listed.)

1975-08-05

Filing date

1975-08-05

Publication date

1979-04-10

1975-08-05 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1975-08-05 Priority to CA232,871A priority Critical patent/CA1052377A/fr

1979-04-10 Application granted granted Critical

1979-04-10 Publication of CA1052377A publication Critical patent/CA1052377A/fr

Status Expired legal-status Critical Current

Links

NAKDJXIEBCHXIZ-UHFFFAOYSA-N dihydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(=S)C1=CC=CC=C1 NAKDJXIEBCHXIZ-UHFFFAOYSA-N 0.000 title claims abstract description 4
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title description 2
150000003512 tertiary amines Chemical class 0.000 claims abstract description 15
239000003054 catalyst Substances 0.000 claims abstract description 14
239000007788 liquid Substances 0.000 claims abstract description 14
-1 alkali metal salts Chemical class 0.000 claims abstract description 13
150000004714 phosphonium salts Chemical class 0.000 claims abstract description 10
239000012429 reaction media Substances 0.000 claims abstract description 10
150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 9
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
230000000269 nucleophilic effect Effects 0.000 claims abstract description 4
125000002837 carbocyclic group Chemical class 0.000 claims abstract description 3
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 10
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 6
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 3
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 3
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 2
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims 1
HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 abstract description 4
230000035484 reaction time Effects 0.000 abstract description 4
VKIRSJUQKXHQCS-UHFFFAOYSA-N chloro-hydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical class OP(Cl)(=S)C1=CC=CC=C1 VKIRSJUQKXHQCS-UHFFFAOYSA-N 0.000 abstract description 2
125000006615 aromatic heterocyclic group Chemical class 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
239000011734 sodium Substances 0.000 description 12
150000001412 amines Chemical class 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
229940073584 methylene chloride Drugs 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000012216 screening Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical group CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
GSOZVENRSFXLPV-UHFFFAOYSA-N 1-butyl-1h-pyrrol-1-ium;chloride Chemical class [Cl-].CCCC[NH+]1C=CC=C1 GSOZVENRSFXLPV-UHFFFAOYSA-N 0.000 description 1
INJKWASQTISCEJ-UHFFFAOYSA-M 1-hexylpyridin-1-ium;iodide Chemical compound [I-].CCCCCC[N+]1=CC=CC=C1 INJKWASQTISCEJ-UHFFFAOYSA-M 0.000 description 1
ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 description 1
QAIGYXWRIHZZAA-UHFFFAOYSA-M 1-methylpyridin-1-ium;chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1 QAIGYXWRIHZZAA-UHFFFAOYSA-M 0.000 description 1
ADSOSINJPNKUJK-UHFFFAOYSA-N 2-butylpyridine Chemical compound CCCCC1=CC=CC=N1 ADSOSINJPNKUJK-UHFFFAOYSA-N 0.000 description 1
QXFJJCJBDOXWDA-UHFFFAOYSA-M 4,4-dibutylmorpholin-4-ium;chloride Chemical compound [Cl-].CCCC[N+]1(CCCC)CCOCC1 QXFJJCJBDOXWDA-UHFFFAOYSA-M 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
150000000565 5-membered heterocyclic compounds Chemical class 0.000 description 1
150000000644 6-membered heterocyclic compounds Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910001514 alkali metal chloride Inorganic materials 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical group CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
OZXRLJIEKITDLN-UHFFFAOYSA-M benzyl(triethyl)phosphanium;chloride Chemical compound [Cl-].CC[P+](CC)(CC)CC1=CC=CC=C1 OZXRLJIEKITDLN-UHFFFAOYSA-M 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical group C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
239000003139 biocide Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003518 caustics Substances 0.000 description 1
RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical group CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000006377 halopyridyl group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
YQRNTVUSJHYLNZ-UHFFFAOYSA-N methyl(tridecyl)azanium;chloride Chemical class [Cl-].CCCCCCCCCCCCC[NH2+]C YQRNTVUSJHYLNZ-UHFFFAOYSA-N 0.000 description 1
TUKHEGNEOVJITQ-UHFFFAOYSA-M methyl(triphenyl)azanium;fluoride Chemical compound [F-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 TUKHEGNEOVJITQ-UHFFFAOYSA-M 0.000 description 1
QRPRIOOKPZSVFN-UHFFFAOYSA-M methyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 QRPRIOOKPZSVFN-UHFFFAOYSA-M 0.000 description 1
ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical group CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
FPPYFDBIUGVMNA-UHFFFAOYSA-N n,n-diethyl-3-phenylpropan-1-amine Chemical compound CCN(CC)CCCC1=CC=CC=C1 FPPYFDBIUGVMNA-UHFFFAOYSA-N 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
KRQVHVYCSNYVCS-UHFFFAOYSA-N n,n-dimethylmethanamine;1-methylpyrrolidine Chemical compound CN(C)C.CN1CCCC1 KRQVHVYCSNYVCS-UHFFFAOYSA-N 0.000 description 1
ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
REXOFKYWPCKVIN-UHFFFAOYSA-N pyridin-2-yl dihydrogen phosphate Chemical class OP(O)(=O)OC1=CC=CC=N1 REXOFKYWPCKVIN-UHFFFAOYSA-N 0.000 description 1
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
CSYKMPIRLUANIQ-UHFFFAOYSA-M sodium;3,5,6-trichloropyridine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=NC(Cl)=C(Cl)C=C1Cl CSYKMPIRLUANIQ-UHFFFAOYSA-M 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
CCBCJOPAGXYIQL-UHFFFAOYSA-M tetrabenzylazanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C[N+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 CCBCJOPAGXYIQL-UHFFFAOYSA-M 0.000 description 1
BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical class CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 0.000 description 1
KUSDSMLUXMFMCB-UHFFFAOYSA-M trimethyl(2-phenylethyl)azanium;chloride Chemical class [Cl-].C[N+](C)(C)CCC1=CC=CC=C1 KUSDSMLUXMFMCB-UHFFFAOYSA-M 0.000 description 1
YCYOWIYHCRGAAH-UHFFFAOYSA-M trimethyl(naphthalen-1-yl)azanium;chloride Chemical compound [Cl-].C1=CC=C2C([N+](C)(C)C)=CC=CC2=C1 YCYOWIYHCRGAAH-UHFFFAOYSA-M 0.000 description 1
GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
DGOVSCVARCXHRS-UHFFFAOYSA-M trimethyl-(4-methylphenyl)azanium;chloride Chemical compound [Cl-].CC1=CC=C([N+](C)(C)C)C=C1 DGOVSCVARCXHRS-UHFFFAOYSA-M 0.000 description 1
UMMDBKGUDMBUSR-UHFFFAOYSA-M tris-decyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC UMMDBKGUDMBUSR-UHFFFAOYSA-M 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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Catalysts (AREA)

CA232,871A 1975-08-05 1975-08-05 Procede pour la preparation de phosphorothioates et de phenylphosphonothioates Expired CA1052377A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA232,871A CA1052377A (fr)	1975-08-05	1975-08-05	Procede pour la preparation de phosphorothioates et de phenylphosphonothioates

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA232,871A CA1052377A (fr)	1975-08-05	1975-08-05	Procede pour la preparation de phosphorothioates et de phenylphosphonothioates

Publications (1)

Publication Number	Publication Date
CA1052377A true CA1052377A (fr)	1979-04-10

Family

ID=4103777

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA232,871A Expired CA1052377A (fr)	1975-08-05	1975-08-05	Procede pour la preparation de phosphorothioates et de phenylphosphonothioates

Country Status (1)

Country	Link
CA (1)	CA1052377A (fr)

1975
- 1975-08-05 CA CA232,871A patent/CA1052377A/fr not_active Expired

Publication	Publication Date	Title
US4096210A (en)	1978-06-20	Process for preparing phosphorothioates and phenylphosphonothioates
CA1065850A (fr)	1979-11-06	Procede d'alkylation pour la preparation d'esters phenoliques disubstitues en n de type carbamate et solution ionique utilisee dans ce procede
US6465643B1 (en)	2002-10-15	Aminophosphonium compounds
CA1052377A (fr)	1979-04-10	Procede pour la preparation de phosphorothioates et de phenylphosphonothioates
US3972887A (en)	1976-08-03	Process for preparing phosphorothioates and phenylphosponothioates
US4147866A (en)	1979-04-03	Process for preparing phosphorothioates and phenylphosphonothioates
US4362885A (en)	1982-12-07	Process for the manufacture of (iodoorganyl)alkoxysilanes
CA1169082A (fr)	1984-06-12	Methode de synthese d'oxydes de phosphine tertiaire; nouveaux oxydes de phosphine tertiaire obtenus
US4092312A (en)	1978-05-30	Process for preparing phosphorothioates and phenylphosphonothioates
US3907815A (en)	1975-09-23	Process for preparing phosphorothioates and phenylphosphonothioates
US5057633A (en)	1991-10-15	Synthesis of perfluoroalkyl bromides
US4016225A (en)	1977-04-05	Process for preparing phosphorothioates and phenylphosphonothioates
US5120846A (en)	1992-06-09	Process for preparing phosphorothioates and phosphonoates in a three-phase system
JPS5920680B2 (ja)	1984-05-15	ホスホロチオエ−トまたはフエニルホスホロチオエ−トを製造する方法
US4418017A (en)	1983-11-29	Preparation of phenylacetonitriles carrying basic substituents
US4866183A (en)	1989-09-12	Preparation of hexaarylbisimidazoles
US3917621A (en)	1975-11-04	Process for preparing phosphorothioates and phenylphosphonothioates
US4144265A (en)	1979-03-13	Process for the manufacture of m-trifluoromethyl benzyl nitrile
US4605784A (en)	1986-08-12	Process for the preparation of ether-containing chlorides
DE2534733C2 (de)	1982-12-16	Verfahren zur Herstellung von Thionophosphorsäureestern und Phenylthionophosphonsäureestern
US6051714A (en)	2000-04-18	Processes for dechlorinating pyridines
JPH0123467B2 (fr)	1989-05-02
US3074993A (en)	1963-01-22	Phosphorotriamidohalidothioates
US4391992A (en)	1983-07-05	N-Denitration of N,2,6-trinitroanilines with phase transfer catalysts
US4481151A (en)	1984-11-06	Process for the preparation of dialkylphosphinic acid halides