DE2247384B2 - Verfahren zur Herstellung von Di(C2 -4 -halogenalkyl) KC2 -4 -halogenalkyl) -phosphonaten durch Umlagerung von TrIs-(C2 -4 -halogenalkyl)phosphiten bei erhöhter Temperatur - Google Patents
Verfahren zur Herstellung von Di(C2 -4 -halogenalkyl) KC2 -4 -halogenalkyl) -phosphonaten durch Umlagerung von TrIs-(C2 -4 -halogenalkyl)phosphiten bei erhöhter TemperaturInfo
- Publication number
- DE2247384B2 DE2247384B2 DE19722247384 DE2247384A DE2247384B2 DE 2247384 B2 DE2247384 B2 DE 2247384B2 DE 19722247384 DE19722247384 DE 19722247384 DE 2247384 A DE2247384 A DE 2247384A DE 2247384 B2 DE2247384 B2 DE 2247384B2
- Authority
- DE
- Germany
- Prior art keywords
- haloalkyl
- phosphite
- reaction
- tris
- temperature
- 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.)
- Withdrawn
Links
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 20
- 230000008707 rearrangement Effects 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 125000001188 haloalkyl group Chemical group 0.000 title description 6
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 239000007788 liquid Substances 0.000 claims description 17
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 21
- 239000000376 reactant Substances 0.000 description 11
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 9
- 238000010924 continuous production Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- -1 carboxy ester Chemical class 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RZIHJXIUVJCZNI-UHFFFAOYSA-N tris(2-bromopropyl) phosphite Chemical compound CC(Br)COP(OCC(C)Br)OCC(C)Br RZIHJXIUVJCZNI-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000004087 circulation Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- XXIDKSWYSYEFAG-UHFFFAOYSA-N 1-chloro-2-[2-chloroethoxy(2-chloroethyl)phosphoryl]oxyethane Chemical compound ClCCOP(=O)(CCCl)OCCCl XXIDKSWYSYEFAG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CTNKMFCADRXINY-UHFFFAOYSA-N tris(2-bromoethyl) phosphite Chemical compound BrCCOP(OCCBr)OCCBr CTNKMFCADRXINY-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ICTZKEXYDDZZFP-SRVKXCTJSA-N Pro-Arg-Pro Chemical compound N([C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(O)=O)C(=O)[C@@H]1CCCN1 ICTZKEXYDDZZFP-SRVKXCTJSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229940058344 antitrematodals organophosphorous compound Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004997 halocarbonyl group Chemical group 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000005648 named reaction Methods 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000101 thioether group Chemical group 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
- C07F9/28—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
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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)
- Fireproofing Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18490571A | 1971-09-29 | 1971-09-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2247384A1 DE2247384A1 (de) | 1973-04-05 |
| DE2247384B2 true DE2247384B2 (de) | 1979-04-19 |
Family
ID=22678812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722247384 Withdrawn DE2247384B2 (de) | 1971-09-29 | 1972-09-27 | Verfahren zur Herstellung von Di(C2 -4 -halogenalkyl) KC2 -4 -halogenalkyl) -phosphonaten durch Umlagerung von TrIs-(C2 -4 -halogenalkyl)phosphiten bei erhöhter Temperatur |
Country Status (8)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3483279A (en) * | 1966-03-11 | 1969-12-09 | Dow Chemical Co | Michaelis-arbuzov reaction |
-
1972
- 1972-08-28 CA CA150,395A patent/CA983046A/en not_active Expired
- 1972-09-08 GB GB4179272A patent/GB1405288A/en not_active Expired
- 1972-09-25 CH CH1397472A patent/CH587279A5/xx not_active IP Right Cessation
- 1972-09-26 FR FR7233987A patent/FR2154590B1/fr not_active Expired
- 1972-09-27 DE DE19722247384 patent/DE2247384B2/de not_active Withdrawn
- 1972-09-28 NL NL7213137A patent/NL165753C/xx not_active IP Right Cessation
- 1972-09-28 BE BE789396D patent/BE789396A/xx unknown
- 1972-09-28 JP JP9759572A patent/JPS5412453B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA983046A (en) | 1976-02-03 |
| NL165753C (nl) | 1981-05-15 |
| NL7213137A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-04-02 |
| JPS5412453B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-23 |
| NL165753B (nl) | 1980-12-15 |
| FR2154590A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-11 |
| FR2154590B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-03 |
| JPS4840724A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-06-15 |
| CH587279A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-29 |
| GB1405288A (en) | 1975-09-10 |
| BE789396A (fr) | 1973-01-15 |
| DE2247384A1 (de) | 1973-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8230 | Patent withdrawn |