JPH0533959B2 - - Google Patents
Info
- Publication number
- JPH0533959B2 JPH0533959B2 JP62027135A JP2713587A JPH0533959B2 JP H0533959 B2 JPH0533959 B2 JP H0533959B2 JP 62027135 A JP62027135 A JP 62027135A JP 2713587 A JP2713587 A JP 2713587A JP H0533959 B2 JPH0533959 B2 JP H0533959B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alkyl
- phosphorus
- dihalogenophosphane
- producing
- 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 - Fee Related
Links
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 42
- 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 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- 239000011630 iodine Substances 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 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
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 5
- 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
- 150000004820 halides Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 54
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 24
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 18
- 238000005292 vacuum distillation Methods 0.000 description 11
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 238000003756 stirring Methods 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
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 235000014666 liquid concentrate Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant 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
- 230000032683 aging Effects 0.000 description 2
- 239000003905 agrochemical Substances 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
- 239000003063 flame retardant Substances 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
- 230000008569 process Effects 0.000 description 2
- 230000009467 reduction Effects 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
- 229910016467 AlCl 4 Inorganic materials 0.000 description 1
- 239000005922 Phosphane Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 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
- 230000008859 change 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 compound 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 compound 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
- JUWSSMXCCAMYGX-UHFFFAOYSA-N gold platinum Chemical compound [Pt].[Au] JUWSSMXCCAMYGX-UHFFFAOYSA-N 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
- 239000000575 pesticide Substances 0.000 description 1
- 229910000064 phosphane Inorganic materials 0.000 description 1
- 238000004445 quantitative analysis 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 JPS63196593A (ja) | 1988-08-15 |
| JPH0533959B2 true 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) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102035867B1 (ko) * | 2012-11-23 | 2019-10-24 | 서강대학교산학협력단 | 기공 내 요오드 또는 브롬이 포집된 요오드 또는 브롬 함유 제올라이트 복합체 및 이의 용도 |
| 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 |
-
1987
- 1987-02-10 JP JP62027135A patent/JPS63196593A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63196593A (ja) | 1988-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4196289A (en) | Process for producing triallyl isocyanurate | |
| US4778933A (en) | Process for making decabromodiphenyl oxide | |
| EP0270724B1 (en) | Preparation of alkyl trifluoroacetoacetate | |
| JPH0533959B2 (en, 2012) | ||
| US4857238A (en) | Manufacturing method for alkyldihalogenophosphines | |
| JP7359141B2 (ja) | ヘキサフルオロ－１，３－ブタジエンの製造方法 | |
| JPS5835514B2 (ja) | イソシアヌル酸トリアルリルの製造方法 | |
| JPS61249964A (ja) | ３，４，５，６−テトラクロロ−２−トリクロロメチルピリジンに富む混合物の調製方法 | |
| EP0010799B1 (en) | A process for the preparation of 3-azabicyclo(3.1.0)hexane derivatives and modifications thereof | |
| JPH0231076B2 (en, 2012) | ||
| US2734084A (en) | Synthesis of l-halo-z | |
| EP0018481B1 (en) | Process for producing alpha, alpha, alpha-trifluoro-o-toluic fluoride | |
| CN1224405A (zh) | 制备LiPF6的方法 | |
| JP3849837B2 (ja) | 二塩化ジメチルスズの合成方法 | |
| JPS6250459B2 (en, 2012) | ||
| KR100249783B1 (ko) | 염화 카보라노일의 제조방법 | |
| EP0346881B1 (en) | A process for producing furylpropargylcarbinol and a derivate thereof | |
| EP0015606B1 (en) | Process for the preparation of bis-(cyanoethyl)tin dihalides | |
| JPS5835977B2 (ja) | ピバリン酸クロライドと芳香族カルボン酸クロライドの製造法 | |
| JPH01294650A (ja) | エステル化合物の製造方法 | |
| GB2051067A (en) | Process for the Preparation of 3,3-dimethyl-allyl Alcohol | |
| US4324740A (en) | Preparation of 2-phenylethylene phosphonic acid | |
| KR19980024647A (ko) | 아미노페놀의 제조방법 | |
| KR830001065B1 (ko) | α, α, α-트리플루오로-0-톨루익플루오라이드의 제조방법 | |
| EP0015577A1 (en) | Process for producing 1,1,3,3-tetrafluoro-1,3-dihydro-isobenzofuran |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |