DE2417143C2 - Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern - Google Patents
Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureesternInfo
- Publication number
- DE2417143C2 DE2417143C2 DE2417143A DE2417143A DE2417143C2 DE 2417143 C2 DE2417143 C2 DE 2417143C2 DE 2417143 A DE2417143 A DE 2417143A DE 2417143 A DE2417143 A DE 2417143A DE 2417143 C2 DE2417143 C2 DE 2417143C2
- Authority
- DE
- Germany
- Prior art keywords
- acid ester
- chlorine
- reaction
- dimethyl
- carbon atoms
- 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 claims description 19
- 150000002148 esters Chemical class 0.000 title claims description 17
- 239000002253 acid Substances 0.000 title claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 8
- 239000011574 phosphorus Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000460 chlorine Substances 0.000 description 44
- 229910052760 oxygen Inorganic materials 0.000 description 34
- 229910052801 chlorine Inorganic materials 0.000 description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000009835 boiling Methods 0.000 description 24
- -1 alkoxy radical Chemical class 0.000 description 21
- 125000001309 chloro group Chemical group Cl* 0.000 description 18
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000004508 fractional distillation Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 150000003014 phosphoric acid esters Chemical class 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 9
- 229940050176 methyl chloride Drugs 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 5
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- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
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- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
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- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical group CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical group CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
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- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
-
- 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
-
- 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
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)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2417143A DE2417143C2 (de) | 1974-04-09 | 1974-04-09 | Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern |
| US05/557,725 US3980738A (en) | 1974-04-09 | 1975-03-12 | Process for the preparation of (thio)phosphoric (phosphonic) acid esters |
| SU752116856A SU609471A3 (ru) | 1974-04-09 | 1975-03-27 | Способ получени эфиров кислот фосфора |
| IT22083/75A IT1034906B (it) | 1974-04-09 | 1975-04-07 | Processo per la produzione di esteri tio fosforici fosfonii |
| LU72227A LU72227A1 (US20050027105A9-20050203-C00082.png) | 1974-04-09 | 1975-04-07 | |
| NL7504121A NL7504121A (nl) | 1974-04-09 | 1975-04-07 | Werkwijze voor het bereiden van (thio)fosfor- (fosfon)zuuresters. |
| DD185272A DD119238A5 (US20050027105A9-20050203-C00082.png) | 1974-04-09 | 1975-04-07 | |
| TR18181A TR18181A (tr) | 1974-04-09 | 1975-04-07 | (tio) fosforik (fosfonik) aist esterlerinin imaline mahsus usul |
| CH437875A CH602771A5 (US20050027105A9-20050203-C00082.png) | 1974-04-09 | 1975-04-07 | |
| BE155137A BE827620A (fr) | 1974-04-09 | 1975-04-07 | Procede de production d'esters d'acides (thio) phosphoriques ou (thio)phosponiques |
| IL47029A IL47029A (en) | 1974-04-09 | 1975-04-07 | Process for the preparation of phosphoric phosphonic thiophosphoric and thiophosphonic acid esters |
| AT259775A AT330798B (de) | 1974-04-09 | 1975-04-07 | Verfahren zur herstellung von (thio)phosphor-(phosphon)-saureestern |
| RO7581927A RO65814A (ro) | 1974-04-09 | 1975-04-08 | Procedeu pentru prepararea unor esteri ai acidului (tio)-fosforic si a unor esteri ai acidului (tio)-fosfonic |
| DK149975A DK149975A (US20050027105A9-20050203-C00082.png) | 1974-04-09 | 1975-04-08 | |
| ZA00752223A ZA752223B (en) | 1974-04-09 | 1975-04-08 | Process for the preparation of (thio) phosphoric (phosphonic) acid esters |
| ES436395A ES436395A1 (es) | 1974-04-09 | 1975-04-08 | Procedimiento para preparar esteres de acidos fosforicos, tiofosforicos, fosfonicos y tiofosfonicos. |
| GB1432875A GB1470476A (en) | 1974-04-09 | 1975-04-08 | Process for the preparation of -thio-phosphoric-phosphonic- acid esters |
| IE786/75A IE40969B1 (en) | 1974-04-09 | 1975-04-08 | Process for the preparation of (thio)-phosphoric (phosphonic) acid esters |
| HU75BA00003241A HU171859B (hu) | 1974-04-09 | 1975-04-09 | Novyj sposob poluchenija /tio/-fosforno/fosforno/ kislykh slozhnykh ehfirov |
| JP50042420A JPS5829795B2 (ja) | 1974-04-09 | 1975-04-09 | （ チオ ） リンサン （ ホスホンサン ） エステルノ セイゾウホウホウ |
| AU79997/75A AU483882B2 (en) | 1974-04-09 | 1975-04-09 | Process for the preparation of thio phosphoric (phosphonic) acid esters |
| FR7511073A FR2267324B1 (US20050027105A9-20050203-C00082.png) | 1974-04-09 | 1975-04-09 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2417143A DE2417143C2 (de) | 1974-04-09 | 1974-04-09 | Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2417143A1 DE2417143A1 (de) | 1975-11-06 |
| DE2417143C2 true DE2417143C2 (de) | 1982-04-15 |
Family
ID=5912517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2417143A Expired DE2417143C2 (de) | 1974-04-09 | 1974-04-09 | Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern |
Country Status (21)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2507779C2 (de) * | 1975-02-22 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Phosphorsäureesterhalogenide sowie Verfahren zu deren Herstellung |
| US4138452A (en) * | 1975-02-22 | 1979-02-06 | Bayer Aktiengesellschaft | Process for preparing phosphoric acid esterhalides |
| DE2528996C2 (de) * | 1975-06-28 | 1982-12-30 | Bayer Ag, 5090 Leverkusen | 1-Fluor-2-halogen-äthyl-phosphor (phosphon)säureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematizide |
| DE2630561A1 (de) * | 1976-07-07 | 1978-01-19 | Bayer Ag | 1-fluor-2-halogen-aethyl-thionophosphor (phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
| DE2738508A1 (de) * | 1977-08-26 | 1979-03-01 | Bayer Ag | N-acetyl-0-(1-fluor-2-chloraethyl)- thionophosphor-(phosphon)-saeureesteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
| US4374783A (en) * | 1981-05-08 | 1983-02-22 | Hwang Seong T | O,O-Dialkyl-s-(2,3,4-trichloro)butyl thiophosphate |
| JPS6434058U (US20050027105A9-20050203-C00082.png) * | 1987-08-26 | 1989-03-02 | ||
| US6030961A (en) * | 1997-03-11 | 2000-02-29 | Bar-Ilan Research & Development Co., Ltd. | Oxyalkylene phosphate compounds and uses thereof |
| CN103880881B (zh) * | 2014-04-16 | 2016-05-18 | 苏州科技学院相城研究院 | 一种烯丙基膦酸二甲酯的制备方法 |
| WO2019016903A1 (ja) * | 2017-07-19 | 2019-01-24 | 宇部興産株式会社 | 非水電解液及びそれを用いた蓄電デバイス |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3691275A (en) * | 1969-12-29 | 1972-09-12 | Universal Oil Prod Co | Diesters of halo-substituted alkylphosphonates |
-
1974
- 1974-04-09 DE DE2417143A patent/DE2417143C2/de not_active Expired
-
1975
- 1975-03-12 US US05/557,725 patent/US3980738A/en not_active Expired - Lifetime
- 1975-03-27 SU SU752116856A patent/SU609471A3/ru active
- 1975-04-07 CH CH437875A patent/CH602771A5/xx not_active IP Right Cessation
- 1975-04-07 LU LU72227A patent/LU72227A1/xx unknown
- 1975-04-07 IL IL47029A patent/IL47029A/en unknown
- 1975-04-07 NL NL7504121A patent/NL7504121A/xx not_active Application Discontinuation
- 1975-04-07 DD DD185272A patent/DD119238A5/xx unknown
- 1975-04-07 IT IT22083/75A patent/IT1034906B/it active
- 1975-04-07 TR TR18181A patent/TR18181A/xx unknown
- 1975-04-07 AT AT259775A patent/AT330798B/de not_active IP Right Cessation
- 1975-04-07 BE BE155137A patent/BE827620A/xx not_active IP Right Cessation
- 1975-04-08 GB GB1432875A patent/GB1470476A/en not_active Expired
- 1975-04-08 ES ES436395A patent/ES436395A1/es not_active Expired
- 1975-04-08 ZA ZA00752223A patent/ZA752223B/xx unknown
- 1975-04-08 DK DK149975A patent/DK149975A/da not_active IP Right Cessation
- 1975-04-08 IE IE786/75A patent/IE40969B1/xx unknown
- 1975-04-08 RO RO7581927A patent/RO65814A/ro unknown
- 1975-04-09 HU HU75BA00003241A patent/HU171859B/hu unknown
- 1975-04-09 JP JP50042420A patent/JPS5829795B2/ja not_active Expired
- 1975-04-09 FR FR7511073A patent/FR2267324B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1470476A (en) | 1977-04-14 |
| IT1034906B (it) | 1979-10-10 |
| DK149975A (US20050027105A9-20050203-C00082.png) | 1975-10-10 |
| SU609471A3 (ru) | 1978-05-30 |
| DD119238A5 (US20050027105A9-20050203-C00082.png) | 1976-04-12 |
| IL47029A0 (en) | 1975-06-25 |
| LU72227A1 (US20050027105A9-20050203-C00082.png) | 1976-03-02 |
| FR2267324B1 (US20050027105A9-20050203-C00082.png) | 1978-09-22 |
| US3980738A (en) | 1976-09-14 |
| IL47029A (en) | 1977-12-30 |
| IE40969B1 (en) | 1979-09-26 |
| RO65814A (ro) | 1980-06-15 |
| HU171859B (hu) | 1978-04-28 |
| ES436395A1 (es) | 1977-02-01 |
| TR18181A (tr) | 1978-02-26 |
| BE827620A (fr) | 1975-10-07 |
| AT330798B (de) | 1976-07-26 |
| NL7504121A (nl) | 1975-10-13 |
| JPS50142516A (US20050027105A9-20050203-C00082.png) | 1975-11-17 |
| ATA259775A (de) | 1975-10-15 |
| CH602771A5 (US20050027105A9-20050203-C00082.png) | 1978-07-31 |
| IE40969L (en) | 1975-10-09 |
| JPS5829795B2 (ja) | 1983-06-24 |
| FR2267324A1 (US20050027105A9-20050203-C00082.png) | 1975-11-07 |
| DE2417143A1 (de) | 1975-11-06 |
| AU7999775A (en) | 1976-10-14 |
| ZA752223B (en) | 1976-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |