JPS63196593A - アルキルジハロゲノホスフアンの製造法 - Google Patents
アルキルジハロゲノホスフアンの製造法Info
- Publication number
- JPS63196593A JPS63196593A JP62027135A JP2713587A JPS63196593A JP S63196593 A JPS63196593 A JP S63196593A JP 62027135 A JP62027135 A JP 62027135A JP 2713587 A JP2713587 A JP 2713587A JP S63196593 A JPS63196593 A JP S63196593A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- phosphorus
- producing
- alkyldihalogenophosphane
- chloride
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 125000000217 alkyl group Chemical group 0.000 title claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 41
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 claims description 31
- 239000007795 chemical reaction product Substances 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 22
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 239000011630 iodine Substances 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 238000006722 reduction reaction Methods 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 229940050176 methyl chloride Drugs 0.000 claims description 5
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 3
- 229960003750 ethyl chloride Drugs 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 3
- 239000002798 polar solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 59
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 25
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 14
- 238000004821 distillation Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical class CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000005292 vacuum distillation Methods 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 235000014666 liquid concentrate Nutrition 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- -1 alkyl dichlorophosphanes Chemical class 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- BPQGJGHGCWPAFA-UHFFFAOYSA-N dibromo(methyl)phosphane Chemical class CP(Br)Br BPQGJGHGCWPAFA-UHFFFAOYSA-N 0.000 description 1
- JLUMKVGIQTWWKK-UHFFFAOYSA-N dichloro(chloromethyl)phosphane Chemical compound ClCP(Cl)Cl JLUMKVGIQTWWKK-UHFFFAOYSA-N 0.000 description 1
- JHNJGLVSPIMBLD-UHFFFAOYSA-N dichloro(ethyl)phosphane Chemical class CCP(Cl)Cl JHNJGLVSPIMBLD-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- UPIXZLGONUBZLK-UHFFFAOYSA-N platinum Chemical compound [Pt].[Pt] UPIXZLGONUBZLK-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62027135A JPS63196593A (ja) | 1987-02-10 | 1987-02-10 | アルキルジハロゲノホスフアンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62027135A JPS63196593A (ja) | 1987-02-10 | 1987-02-10 | アルキルジハロゲノホスフアンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63196593A true JPS63196593A (ja) | 1988-08-15 |
| JPH0533959B2 JPH0533959B2 (en, 2012) | 1993-05-20 |
Family
ID=12212609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62027135A Granted JPS63196593A (ja) | 1987-02-10 | 1987-02-10 | アルキルジハロゲノホスフアンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63196593A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016505360A (ja) * | 2012-11-23 | 2016-02-25 | ソガン ユニバーシティ リサーチ ファウンデーションＳｏｇａｎｇ Ｕｎｉｖｅｒｓｉｔｙ Ｒｅｓｅａｒｃｈ Ｆｏｕｎｄａｔｉｏｎ | 気孔内にヨウ素（Ｉ２）又は臭素（Ｂｒ２）が捕集されたヨウ素又は臭素含有のゼオライト複合体とその用途 |
| CN113512063A (zh) * | 2021-08-19 | 2021-10-19 | 四川福思达生物技术开发有限责任公司 | 一种甲基二氯化磷的制备系统及方法 |
-
1987
- 1987-02-10 JP JP62027135A patent/JPS63196593A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016505360A (ja) * | 2012-11-23 | 2016-02-25 | ソガン ユニバーシティ リサーチ ファウンデーションＳｏｇａｎｇ Ｕｎｉｖｅｒｓｉｔｙ Ｒｅｓｅａｒｃｈ Ｆｏｕｎｄａｔｉｏｎ | 気孔内にヨウ素（Ｉ２）又は臭素（Ｂｒ２）が捕集されたヨウ素又は臭素含有のゼオライト複合体とその用途 |
| CN113512063A (zh) * | 2021-08-19 | 2021-10-19 | 四川福思达生物技术开发有限责任公司 | 一种甲基二氯化磷的制备系统及方法 |
| CN113512063B (zh) * | 2021-08-19 | 2024-04-02 | 四川福思达生物技术开发有限责任公司 | 一种甲基二氯化磷的制备系统及方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0533959B2 (en, 2012) | 1993-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0656413A (ja) | 六フッ化リン酸塩の製造方法 | |
| JP3204641B2 (ja) | オキシジフタル酸無水物の製造方法 | |
| JP2006518734A (ja) | 重炭酸塩を触媒として用いるオキシジフタル酸無水物の製造方法 | |
| US5399780A (en) | Method of producing triarylborane | |
| JPS63196593A (ja) | アルキルジハロゲノホスフアンの製造法 | |
| JPS5835514B2 (ja) | イソシアヌル酸トリアルリルの製造方法 | |
| US4036889A (en) | Process for preparing triarylphosphines | |
| US6476271B2 (en) | Process for the preparation of ether-free salts of tetrakis(pentafluorophenyl) borate | |
| JP2558497B2 (ja) | アルキルジハロゲノホスファンの製造法 | |
| US7468174B2 (en) | Method for producing chlorosulfonyl isocyanate | |
| JPS5940838B2 (ja) | エチルバナデ−トの改良製造方法 | |
| CN112154133A (zh) | 六氟-1,3-丁二烯的制造方法 | |
| JP2856655B2 (ja) | トリアリールホウ素の製造方法 | |
| JPS632943B2 (en, 2012) | ||
| US4151186A (en) | Preparation of acyl chlorides | |
| RU2083582C1 (ru) | Способ получения бис-ареновых производных ванадия из оксихлорида ванадия | |
| JP4288715B2 (ja) | トリス（ジブロモプロピル）イソシアヌレートの製造方法 | |
| JPH07242682A (ja) | ジハロゲノアルキルホスファンの製造法 | |
| CN113105492B (zh) | 三氟甲基三甲基硅烷的制备方法 | |
| JPH05125017A (ja) | ピバリン酸クロロメチルエステルの製造法 | |
| CN1224405A (zh) | 制备LiPF6的方法 | |
| US3963751A (en) | Chlorination of butadiene sulfone to 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxide | |
| JPH03218917A (ja) | 三塩化ホウ素の製造方法 | |
| US2670363A (en) | Preparation of titanium chloride acetate powder material | |
| JPH11171825A (ja) | 塩化ベンゾイルの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |