EP3221325A1 - Method for producing methyl-dichloro-phosphane - Google Patents
Method for producing methyl-dichloro-phosphaneInfo
- Publication number
- EP3221325A1 EP3221325A1 EP15798015.2A EP15798015A EP3221325A1 EP 3221325 A1 EP3221325 A1 EP 3221325A1 EP 15798015 A EP15798015 A EP 15798015A EP 3221325 A1 EP3221325 A1 EP 3221325A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pci3
- range
- mdp
- amount
- mol
- 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- Withdrawn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
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 38
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000010574 gas phase reaction Methods 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 16
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/45—Compounds containing sulfur and halogen, with or without oxygen
- C01B17/4561—Compounds containing sulfur, halogen and oxygen only
- C01B17/4584—Thionyl chloride (SOCl2)
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/45—Compounds containing sulfur and halogen, with or without oxygen
- C01B17/4561—Compounds containing sulfur, halogen and oxygen only
- C01B17/4592—Sulfuryl chloride (SO2Cl2)
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/52—Halophosphines
Definitions
- the present invention relates primarily to a process for the preparation of methyldichlorophosphine (MDP) by reacting methane with PCI3 (phosphorus trichloride) in the presence of a catalytically effective amount of a compound of formula SO x Cb, wherein the index x is 1 (SOCb, thionyl chloride) or 2 (SO 2 Cl 2, sulfuryl chloride).
- MDP methyldichlorophosphine
- EP 0999216 A2 describes a process for preparing aliphatic alkyldihalophosphanes by reacting an aliphatic hydrocarbon with a phosphorus trihalide, wherein the reaction is initiated photochemically with a UV excimer radiation source.
- US 2137792 relates to the reaction of alkanes with more than 5 carbon atoms with phosphorus trichloride using aluminum trichloride to the corresponding Alkyldihalogenphosphan- aluminum trichloride complexes, from which then the corresponding Alkyldihalogenphosphan can be released.
- No. 3,210,418 describes the synthesis of alkyldihalophosphanes by reacting alkanes with phosphorus trihalides with the addition of catalytic amounts of atmospheric oxygen as initiator.
- US 3709932 describes a process for the conversion of alkanes with phosphorus trihalides to alkyl dihalophosphanes in the presence of catalytic amounts of phosgene.
- US 3974217 discloses a process for the synthesis of substituted phenylphosphoredihalides by reacting substituted phenylene with phosphorus trihalides in the presence of catalytic amounts of tin tetrachloride or titanium tetrachloride.
- EP 0082350 Al relates to the preparation of methyldichlorophosphane by reacting methane with phosphorus trichloride in the presence of 2 to 7 mol% carbon tetrachloride, calculated on the phosphorus trichloride used, at temperatures of 500 to 650 ° C and a residence time of 0.1 to 0.9 s wherein the reaction is carried out at a pressure of 2 to 10 bar and with increasing pressure, the added amount of carbon tetrachloride is reduced.
- CCLt carbon tetrachloride
- the primary object of the present invention was to find an alternative to the use of carbon tetrachloride in the process for producing MDP from PCI3 and methane.
- the invention therefore primarily relates to a process for the preparation of methyldichlorophosphine by reacting methane with phosphorus trichloride, characterized in that the reaction takes place in the presence of a compound of the formula SOxCb, where x is 1 or 2.
- the method according to the invention can be represented schematically as follows, wherein the index x can assume the values 1 (one) or 2 (two): SO x CI 2
- the process according to the invention is preferably carried out in the presence of a catalytically effective amount of a compound of the formula SO x Ck, where x is 1 or 2.
- the process of the invention is preferably carried out in the presence of a catalytically effective amount of thionyl chloride and / or sulfuryl chloride.
- the total amount of SOxCk is preferably in the range of 0.1 to 10 mol%, preferably in the range of 0.5 to 9 mol%, more preferably in the range of 1 to 8 mol%, particularly preferably in the range of 2 to 8 mol%, and most preferably in the range of 3 to 7 mol%, in each case based on the amount of PCI3 used.
- the inventive method is preferably carried out at a temperature in the range of 400 ° C to 750 ° C, preferably at a temperature in the range of 420 ° C to 700 ° C, more preferably at a temperature in the range of 450 ° C to 650 ° C. ,
- the molar ratio (mol / mol) of CH4 and PCI3 in the process according to the invention is preferably in the range from 12: 1 to 2: 1, preferably in the range from 10: 1 to 3: 1, and particularly preferably in the range from 8: 1 to 4: 1.
- the inventive method is preferably carried out at a reaction pressure in the range of 500 mbar and 25 bar, preferably at a reaction pressure in the range of 700 mbar and 12 bar, more preferably at a reaction pressure in the range of 900 mbar and 10 bar.
- the process according to the invention is preferably carried out in such a way that the conversion of CH 4 and PCI 3 to MDP takes place in a gas phase reaction.
- the process according to the invention is preferably carried out by reacting a homogeneous mixture comprising CH4, PCI3 and SOxCk in a gas phase reaction to form MDP.
- the average residence time of the reaction components CH4, PCI3 and SOxCk, preferably of the homogeneous mixture of CH4, PCI3 and SOxCk, in the reaction space is preferably in the range from 0.05 to 60 seconds, preferably in the range from 0.1 to 10 seconds, more preferably in Range of 0.5 to 5 seconds.
- the inventive method is carried out in such a way that CH4, PCI3 and SOxCb, preferably in the above or below as preferred or particularly preferred specified amounts (ratios), are reacted in a flow tube. If CH4, PCI3 and SOxCL are reacted in a flow tube, this flow tube preferably has a diameter of at least 5 mm, preferably a diameter of at least 8 mm.
- this flow tube preferably has a length of at least 10 cm, preferably a length of at least 15 cm.
- this flow tube in a further preferred embodiment preferably has a length of at least 100 cm, preferably a length of at least 150 cm.
- preference is given to using SO 2 Cl 2 (sulfuryl chloride) or a mixture of SO 2 Cl 2 (sulfuryl chloride) and SOCL (thionyl chloride) as the catalyst, since even higher yields of methyldichlorophosphane (MDP) can be achieved when using SO 2 Cl 2 (sulfuryl chloride) in the process according to the invention ,
- the inventive method is carried out in such a way that no catalytically effective amounts of elemental oxygen (O2), elemental chlorine (CL), phosgene (COCL), carbon tetrachloride (CCL), nitrogen oxides and chlorinated hydrocarbons are used, and also preferably no UV excimer radiation source is used.
- O2 elemental oxygen
- CL elemental chlorine
- COCL phosgene
- CCL carbon tetrachloride
- nitrogen oxides and chlorinated hydrocarbons are used, and also preferably no UV excimer radiation source is used.
- catalysts SOCL thionyl chloride
- SO 2 Cl 2 sulfuryl chloride
- the present invention relates to the use of a compound of the formula SO x CL, wherein x is 1 or 2, for the preparation of methyldichlorophosphine (MDP), in particular in one of the preferred embodiments of the inventive method for producing methyldichlorophosphane (MDP ).
- MDP methyldichlorophosphine
- the present invention relates to mixtures comprising, essentially, consisting of or consisting of
- (ii) SOxCL where x is 1 or 2, wherein the total amount of component (ii) SOxCh is preferably in the range of 0.1 to 10 mol%, preferably in the range of 0.5 to 9 mol%, more preferably in the range of 1 to 8 mol%, particularly preferably in the range of 2 to 8 mol%, and most preferably in the range of 3 to 7 mol%, in each case based on the amount of component (i) used PCI3.
- a mixture according to the invention consisting essentially of (i) PCI3, and (ii) SOxCh, where x is 1 or 2, preferably refers to a mixture in which the sum of components (i) and (ii) total at least 85 % By weight, preferably at least 90% by weight in total, and particularly preferably at least 95% by weight in total, in each case based on the total weight of the mixture.
- the present invention relates to mixtures comprising, essentially, consisting of or consisting of
- the molar ratio (mol / mol) of component (iii) CH4 and component (i) PCI3 is preferably in the range from 12: 1 to 2: 1, preferably in the range from 10: 1 to 3: 1, and particularly preferably in Range of 8: 1 to 4: 1.
- the total amount of component (ii) SOxCb is preferably in the range of 0.1 to 10 mol%, preferably in the range of 0.5 to 9 mol%, more preferably in the range of 1 to 8 mol%, more preferably in the range of 2 to 8 mol%, and most preferably in the range of 3 to 7 mol%, in each case based on the amount of component (i) used PCI3.
- a mixture according to the invention consisting essentially of (i) PCI3, (ii) SOxCb, where x denotes the value 1 or 2, and (iii) CH 4 is preferably refers to a mixture in which the sum of the components (i), ( ii) and (iii) is at least 90% by weight, preferably at least 95% by weight in total, and particularly preferably at least 98% by weight, in each case based on the total weight of the mixture.
- the present invention relates to mixtures comprising, essentially, consisting of or consisting of
- a mixture according to the invention consisting essentially of (i) PCI3, (ii) SOxCh, wherein x is 1 or 2, (iii) CH 4, and (iv) MDP (Methyldichlorophosphan) preferably refers to a mixture in which the sum the constituents (i), (ii) (iii) and (iv) is at least 80% by weight, preferably at least 90% by total, and particularly preferably at least 95% by weight, based in each case on the total weight of the mixture.
- Measurement methods Measurement methods:
- Hewlett Packard gas chromatograph column: Zebron ZB-624, 30m x 0.53 mm, 3 ⁇ , He, split 20: 1.
- Detector WLD, injection volume: 10 ⁇ , 60 ° C, isothermal, 10 ° C / min , 230 ° C.
- MDP methyldichlorophosphine
- Example 3 The preparation of methyldichlorophosphine (MDP) was carried out according to Example 1, wherein a temperature of 600 ° C was set.
- MDP methyldichlorophosphine
- MDP methyldichlorophosphine
- MDP methyldichlorophosphine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14194201 | 2014-11-20 | ||
PCT/EP2015/076921 WO2016079164A1 (en) | 2014-11-20 | 2015-11-18 | Method for producing methyl-dichloro-phosphane |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3221325A1 true EP3221325A1 (en) | 2017-09-27 |
Family
ID=51999249
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP15798015.2A Withdrawn EP3221325A1 (en) | 2014-11-20 | 2015-11-18 | Method for producing methyl-dichloro-phosphane |
Country Status (10)
Country | Link |
---|---|
US (1) | US20170313731A1 (en) |
EP (1) | EP3221325A1 (en) |
JP (1) | JP2018501205A (en) |
KR (1) | KR20170083552A (en) |
CN (1) | CN107001401A (en) |
BR (1) | BR112017010466A2 (en) |
IL (1) | IL252173A0 (en) |
MX (1) | MX2017006458A (en) |
TW (1) | TW201627316A (en) |
WO (1) | WO2016079164A1 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106117267A (en) * | 2016-06-27 | 2016-11-16 | 安徽国星生物化学有限公司 | A kind of green synthesis method of methyl dichloro phosphorus |
CN110891959B (en) | 2017-07-12 | 2022-10-28 | 株式会社Mmag | Process for producing herbicide intermediate |
CN108329351A (en) * | 2018-02-12 | 2018-07-27 | 邹伟 | A kind of preparation method of alkyl dichloride phosphine |
CN108659042B (en) * | 2018-06-22 | 2020-08-04 | 河北威远生物化工有限公司 | Extraction separation method and extraction rectification equipment of alkyl phosphine dichloride |
CN111320140B (en) * | 2019-02-25 | 2021-08-13 | 江西世龙实业股份有限公司 | Thionyl chloride production system and driving method thereof |
CN114539315B (en) * | 2022-02-28 | 2023-08-25 | 佳木斯黑龙农药有限公司 | Synthesis method of methyl phosphine dichloride |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2137792A (en) | 1936-09-12 | 1938-11-22 | Victor Chemical Works | Organic phosphorus-containing compounds |
US3210418A (en) | 1953-10-19 | 1965-10-05 | Fmc Corp | Preparation of aliphatic dihalophosphines |
US3709932A (en) | 1969-09-22 | 1973-01-09 | Stauffer Chemical Co | Phosphonous dichlorides |
US3974217A (en) | 1974-07-31 | 1976-08-10 | Monsanto Company | Preparation of substituted phenyl phosphonous dichlorides |
FR2336985A1 (en) | 1975-12-31 | 1977-07-29 | Bertucci Albert | FUMES, VAPORS AND GREASE EXHAUST DEVICE, ESPECIALLY FOR RESTAURANT KITCHEN OR COMMUNITY KITCHEN |
DE2629299C2 (en) | 1976-06-30 | 1978-08-24 | Hoechst Ag, 6000 Frankfurt | Process for the production of methyldichlorophosphine |
GB1533200A (en) * | 1976-06-30 | 1978-11-22 | Hoechst Ag | Production of methyldichlorophosphane |
DE3149937A1 (en) | 1981-12-17 | 1983-06-30 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING METHYLDICHLORPHOSPHANE |
DE19840553A1 (en) * | 1998-09-07 | 2000-03-09 | Aventis Res & Tech Gmbh & Co | Photochemical production of alkyl dihalophosphanes in high selectivity from phosphorus halide and hydrocarbon using UV excimer radiation, used e.g. as intermediates for plant protectants |
-
2015
- 2015-11-18 KR KR1020177012767A patent/KR20170083552A/en unknown
- 2015-11-18 WO PCT/EP2015/076921 patent/WO2016079164A1/en active Application Filing
- 2015-11-18 US US15/528,426 patent/US20170313731A1/en not_active Abandoned
- 2015-11-18 TW TW104137988A patent/TW201627316A/en unknown
- 2015-11-18 BR BR112017010466A patent/BR112017010466A2/en not_active Application Discontinuation
- 2015-11-18 JP JP2017527242A patent/JP2018501205A/en not_active Withdrawn
- 2015-11-18 EP EP15798015.2A patent/EP3221325A1/en not_active Withdrawn
- 2015-11-18 CN CN201580063315.3A patent/CN107001401A/en active Pending
- 2015-11-18 MX MX2017006458A patent/MX2017006458A/en unknown
-
2017
- 2017-05-09 IL IL252173A patent/IL252173A0/en unknown
Non-Patent Citations (2)
Title |
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None * |
See also references of WO2016079164A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2018501205A (en) | 2018-01-18 |
CN107001401A (en) | 2017-08-01 |
BR112017010466A2 (en) | 2018-04-03 |
TW201627316A (en) | 2016-08-01 |
MX2017006458A (en) | 2017-09-12 |
US20170313731A1 (en) | 2017-11-02 |
IL252173A0 (en) | 2017-07-31 |
WO2016079164A1 (en) | 2016-05-26 |
KR20170083552A (en) | 2017-07-18 |
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