DD155071A5 - Verfahren zur herstellung von phosphorsaeurepropargylestern - Google Patents

Verfahren zur herstellung von phosphorsaeurepropargylestern Download PDF

Info

Publication number: DD155071A5
Authority: DD; German Democratic Republic
Prior art keywords: phosphoric acid; chloride; mol; propargyl; catalyst
Prior art date: 1979-07-02

Application number

DD80222262A

Other languages

German (de)

English (en)

Inventor

Guenter Arend

Peter Feyen

Original Assignee

Bayer Ag

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.)

1979-07-02

Filing date

1980-06-30

Publication date

1982-05-12

1980-06-30 Application filed by Bayer Ag filed Critical Bayer Ag

1982-05-12 Publication of DD155071A5 publication Critical patent/DD155071A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 26
-1 PHOSPHORIC ACID PROPARGYL ESTERS Chemical class 0.000 title claims abstract description 20
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 13
229910000147 aluminium phosphate Inorganic materials 0.000 title claims abstract description 8
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims abstract description 25
239000003054 catalyst Substances 0.000 claims abstract description 14
239000002253 acid Substances 0.000 claims abstract description 13
150000003512 tertiary amines Chemical class 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
150000007529 inorganic bases Chemical class 0.000 claims abstract description 7
239000002516 radical scavenger Substances 0.000 claims abstract description 7
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
150000004714 phosphonium salts Chemical class 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
125000002091 cationic group Chemical group 0.000 claims 1
SBUAYSSKTAGAGF-UHFFFAOYSA-N prop-2-ynyl dihydrogen phosphate Chemical class OP(O)(=O)OCC#C SBUAYSSKTAGAGF-UHFFFAOYSA-N 0.000 abstract description 7
238000004519 manufacturing process Methods 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
230000000052 comparative effect Effects 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 14
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
238000004821 distillation Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
239000012071 phase Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
BURXZHCIEDSVSW-UHFFFAOYSA-N diethyl prop-2-ynyl phosphate Chemical compound CCOP(=O)(OCC)OCC#C BURXZHCIEDSVSW-UHFFFAOYSA-N 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QAWIVZSNCYVVBC-UHFFFAOYSA-N Cl.Cl.OP(O)(=O)OCC#C Chemical compound Cl.Cl.OP(O)(=O)OCC#C QAWIVZSNCYVVBC-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
238000003756 stirring Methods 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
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 3
ILXZMTJXXHNZJS-UHFFFAOYSA-N diethyl hydrogen phosphate;hydrochloride Chemical compound Cl.CCOP(O)(=O)OCC ILXZMTJXXHNZJS-UHFFFAOYSA-N 0.000 description 3
JASFTUXTUYZCBW-UHFFFAOYSA-N ethyl dihydrogen phosphate;dihydrochloride Chemical compound Cl.Cl.CCOP(O)(O)=O JASFTUXTUYZCBW-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
150000003014 phosphoric acid esters Chemical class 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000011084 recovery Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
239000010409 thin film Substances 0.000 description 2
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
BZUDVELGTZDOIG-UHFFFAOYSA-N 2-ethyl-n,n-bis(2-ethylhexyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CC(CC)CCCC BZUDVELGTZDOIG-UHFFFAOYSA-N 0.000 description 1
WWSYLVQUYMYQBU-UHFFFAOYSA-N 3-[benzyl(2-cyanoethyl)amino]propanenitrile Chemical compound N#CCCN(CCC#N)CC1=CC=CC=C1 WWSYLVQUYMYQBU-UHFFFAOYSA-N 0.000 description 1
WLVNEALRNQEPMS-UHFFFAOYSA-N 3-ethylpentan-3-ylbenzene Chemical compound CCC(CC)(CC)C1=CC=CC=C1 WLVNEALRNQEPMS-UHFFFAOYSA-N 0.000 description 1
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
CUSPWNZNSSHZAK-UHFFFAOYSA-N Cl.C#CCOP(=O)(O)OCC#C Chemical compound Cl.C#CCOP(=O)(O)OCC#C CUSPWNZNSSHZAK-UHFFFAOYSA-N 0.000 description 1
NNGNDJOOEZGKCK-UHFFFAOYSA-N Cl.CCOP(O)(=O)OCC#C Chemical compound Cl.CCOP(O)(=O)OCC#C NNGNDJOOEZGKCK-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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 group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
229960001716 benzalkonium Drugs 0.000 description 1
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
229950010007 dimantine Drugs 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-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
WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
UZJBOHHDWXQTEF-UHFFFAOYSA-N pocl3 pyridine Chemical compound ClP(Cl)(Cl)=O.C1=CC=NC=C1 UZJBOHHDWXQTEF-UHFFFAOYSA-N 0.000 description 1
DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
- 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
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
- 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
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD80222262A 1979-07-02 1980-06-30 Verfahren zur herstellung von phosphorsaeurepropargylestern DD155071A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792926652 DE2926652A1 (de)	1979-07-02	1979-07-02	Verfahren zur herstellung von phosphorsaeurepropargylestern

Publications (1)

Publication Number	Publication Date
DD155071A5 true DD155071A5 (de)	1982-05-12

Family

ID=6074699

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80222262A DD155071A5 (de)	1979-07-02	1980-06-30	Verfahren zur herstellung von phosphorsaeurepropargylestern

Country Status (9)

Country	Link
US (1)	US4327040A (pt)
EP (1)	EP0021361B1 (pt)
JP (1)	JPS5610197A (pt)
BR (1)	BR8004084A (pt)
DD (1)	DD155071A5 (pt)
DE (2)	DE2926652A1 (pt)
DK (1)	DK284980A (pt)
IL (1)	IL60436A0 (pt)
PL (1)	PL225361A1 (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2949391A1 (de) *	1979-12-07	1981-07-16	Bayer Ag, 5090 Leverkusen	Insektizide und akarizide mittel entaltend propargylthionophophorsaeureester
US4472391A (en) *	1980-11-21	1984-09-18	Rhone-Poulenc Agrochimie	O-Aryl-s-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides
US4428945A (en)	1980-11-21	1984-01-31	Rhone-Poulenc Agrochimie	O-Alkyl S-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides
US4472390A (en) *	1980-12-31	1984-09-18	Rhone-Poulenc Agrochimie	S-Alkyls-(tertiary alkyl) alkylphosphonodithioate insecticides and nematocides
US4600791A (en) *	1983-12-12	1986-07-15	Borg-Warner Chemicals, Inc.	Process for preparation of phosphazene esters
KR102616161B1 (ko) *	2021-06-28	2023-12-20	씨에스아이엠 주식회사	리튬이온 전지용 난연제로 유용한 인산 프로파질 에스테르 화합물의 제조방법
CN119391070A (zh) *	2024-11-28	2025-02-07	宁波卡倍亿新材料科技有限公司	一种新能源汽车耐高温阻燃电缆料及其制备方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2471464A (en) *	1947-12-22	1949-05-31	Victor Chemical Works	Method of preparing para nitrophenyl diethyl thionophosphate
US2865801A (en) *	1956-04-06	1958-12-23	Monsanto Chemicals	Propargyl phosphorothioates
US3005001A (en) *	1960-11-14	1961-10-17	Dow Chemical Co	O, o'-(2-butenylene) and (2-butynylene) bis-(o-alkyl phosphoramidothioates)
US3087957A (en) *	1961-07-06	1963-04-30	Dow Chemical Co	O-alkynyl o-alkyl phosphoramidates and phosphoramidothioates
US3189636A (en) *	1961-12-08	1965-06-15	Lubrizol Corp	Allenic phosphorus compounds
US3336422A (en) *	1964-06-18	1967-08-15	American Potash & Chem Corp	Process for producing thiophosphate esters
JPS5242779B1 (pt) *	1969-03-19	1977-10-26
US3972887A (en) *	1972-12-11	1976-08-03	The Dow Chemical Company	Process for preparing phosphorothioates and phenylphosponothioates
US4007197A (en) *	1975-06-10	1977-02-08	The Dow Chemical Company	Process for preparing phosphorothioates and phenylphosphonothioates
NL186814C (nl) *	1975-08-07	1991-03-01	Dow Chemical Co	Werkwijze ter bereiding van een fosforthioaat of fenylfosfonothioaat.
CA1099278A (en) *	1976-12-06	1981-04-14	Raymond A. Simone	Manufacture of substituted phenyl phosphates involving use of phase transfer catalysts
DE2727479A1 (de) *	1977-06-18	1979-01-04	Bayer Ag	Insektizide und akarizide mittel
DE2833341A1 (de) *	1978-07-29	1980-02-14	Bayer Ag	Verfahren zur herstellung von phosphorsaeure-triestern
DE2833342A1 (de) *	1978-07-29	1980-02-14	Bayer Ag	Verfahren zur herstellung neutraler phosphorsaeureester nach dem phasengrenzflaechenverfahren

1979
- 1979-07-02 DE DE19792926652 patent/DE2926652A1/de not_active Withdrawn
1980
- 1980-06-09 US US06/158,032 patent/US4327040A/en not_active Expired - Lifetime
- 1980-06-20 EP EP80103449A patent/EP0021361B1/de not_active Expired
- 1980-06-20 DE DE8080103449T patent/DE3060916D1/de not_active Expired
- 1980-06-30 IL IL60436A patent/IL60436A0/xx unknown
- 1980-06-30 BR BR8004084A patent/BR8004084A/pt unknown
- 1980-06-30 DD DD80222262A patent/DD155071A5/de unknown
- 1980-06-30 JP JP8798180A patent/JPS5610197A/ja active Pending
- 1980-06-30 PL PL22536180A patent/PL225361A1/xx unknown
- 1980-07-01 DK DK284980A patent/DK284980A/da unknown

Also Published As

Publication number	Publication date
PL225361A1 (pt)	1981-06-05
EP0021361B1 (de)	1982-10-06
DK284980A (da)	1981-01-03
BR8004084A (pt)	1981-01-21
US4327040A (en)	1982-04-27
IL60436A0 (en)	1980-09-16
DE3060916D1 (en)	1982-11-11
EP0021361A1 (de)	1981-01-07
JPS5610197A (en)	1981-02-02
DE2926652A1 (de)	1981-01-22

Publication	Publication Date	Title
EP0379914B1 (de)	1993-09-08	Verfahren zur Herstellung von modifizierten, Isocyanuratgruppen ausweisenden Polyisocyanaten und ihre Verwendung
EP0591798B1 (de)	1996-08-28	Verfahren zur Herstellung von O-substituierten Hydroxylammoniumsalzen
DD155071A5 (de)	1982-05-12	Verfahren zur herstellung von phosphorsaeurepropargylestern
WO2017055193A1 (de)	2017-04-06	Verfahren zur Herstellung von Phosphinaten
DE68921340T2 (de)	1995-10-19	Herstellung von epoxinitraten.
EP0105494B1 (de)	1988-08-10	Verfahren zur Herstellung von Benzthiazolyloxyphenoxypropionsäurederivaten
DE2338007B2 (de)	1980-10-16	Verfahren zur Herstellung von Tetrakis-(2-halogenalky))-alkylendiphosphaten
DE19902960A1 (de)	2000-07-27	Verfahren zur Herstellung von Methylcarbazat
DE2538310C3 (de)	1980-08-28	Verfahren zur Herstellung von O.O-Dialkylthionophosphorsäurechloriden
EP0157270B1 (de)	1988-06-15	Verfahren zur Herstellung von tetrachlorierten Benzo-1,4-dioxenen
EP0302331B1 (de)	1992-09-16	Ester von Arylbisperfluoralkylcarbinolen, Verfahren zur Herstellung dieser Verbindungen und der zugrundeliegenden Arylbisperfluoralkylcarbinole
WO2002012209A1 (de)	2002-02-14	Verfahren zur reinigung von 2-chlor-5-chlormethylthiazol
EP2476685B1 (de)	2017-08-02	Verfahren zur Herstellung von Alkylphosphaten
EP1401845B1 (de)	2005-04-13	Verfahren zur herstellung von n-phosphonomethylglycin
DE3881536T2 (de)	1993-09-16	Verfahren zur herstellung von festen polyhalotriarylphosphorsaeureestern.
DE19910463B4 (de)	2007-05-10	Dialkylphosphorsäuren nach der Methanol-Methode
DE2558508B2 (de)	1978-12-07	Verfahren zur Racematspaltung von DL-Pantolacton
DE69017787T2 (de)	1995-10-12	Verfahren zur Herstellung von Methylendi(phenylurethan).
DD139716A5 (de)	1980-01-16	Verfahren zur herstellung von dialkyl-phosphorchloridothionaten
DE60103565T2 (de)	2004-09-16	Verfahren zur herstellung von 2-methoxy-4-methyl-6-methylamino-1,3,5-triazin
DE69323722T2 (de)	1999-07-22	Verfahren zur Gewinnung eines optisch aktiven Alkohols
WO2003000702A1 (de)	2003-01-03	VERFAHREN ZUR HERSTELLUNG VON $G(a) -AMINOPHOSPHONSÄUREN
DE1768132C (de)	1973-02-22	Verfahren zur Herstellung von alpha beta olefinisch ungesättigten Alkyl phosphonsaureestei n
DE1543747B2 (de)	1975-02-06	Verfahren zur Herstellung von bisquartären Alkylammoniumsulfatsalzen
DE1950642C3 (de)	1977-05-26	Verfahren zur Herstellung von Phosphorsäurearylalkylestern