JPH037677B2 - - Google Patents
Info
- Publication number
- JPH037677B2 JPH037677B2 JP57202249A JP20224982A JPH037677B2 JP H037677 B2 JPH037677 B2 JP H037677B2 JP 57202249 A JP57202249 A JP 57202249A JP 20224982 A JP20224982 A JP 20224982A JP H037677 B2 JPH037677 B2 JP H037677B2
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- acid
- carbon atoms
- yield
- phosphonic acid
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PMVVRSKJCGEFIY-UHFFFAOYSA-N methylphosphonous acid Chemical compound CP(O)O PMVVRSKJCGEFIY-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DLCRZIOMEYKFGJ-UHFFFAOYSA-N butan-1-ol;1,4-xylene Chemical group CCCCO.CC1=CC=C(C)C=C1 DLCRZIOMEYKFGJ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical compound ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- -1 hydrogen halides Chemical class 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- NFJDFXLCWHYUOU-UHFFFAOYSA-N 2-ethylhexoxy(methyl)phosphinous acid Chemical compound CCCCC(CC)COP(C)O NFJDFXLCWHYUOU-UHFFFAOYSA-N 0.000 description 1
- SZZYQBMYVUTEQT-UHFFFAOYSA-N 2-methylpropoxy(phenyl)phosphinous acid Chemical compound CC(C)COP(O)C1=CC=CC=C1 SZZYQBMYVUTEQT-UHFFFAOYSA-N 0.000 description 1
- IWTBVKIGCDZRPL-LURJTMIESA-N 3-Methylbutanol Natural products CC[C@H](C)CCO IWTBVKIGCDZRPL-LURJTMIESA-N 0.000 description 1
- XZIRHLQBKIZDDZ-UHFFFAOYSA-N 3-methylbutoxy(phenyl)phosphinous acid Chemical compound CC(C)CCOP(O)C1=CC=CC=C1 XZIRHLQBKIZDDZ-UHFFFAOYSA-N 0.000 description 1
- PODHJIQSMSGBRQ-UHFFFAOYSA-N C1=CC=CC=C1.P(O)(O)=O Chemical class C1=CC=CC=C1.P(O)(O)=O PODHJIQSMSGBRQ-UHFFFAOYSA-N 0.000 description 1
- LZKNMISYQDUSMO-UHFFFAOYSA-N CCP(=O)(O)OCCC(C)C Chemical compound CCP(=O)(O)OCCC(C)C LZKNMISYQDUSMO-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- YOWJRQZLZDBONJ-UHFFFAOYSA-N P.OP(O)=O Chemical class P.OP(O)=O YOWJRQZLZDBONJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- OTXQUGSUXRBUTC-UHFFFAOYSA-N butan-1-ol;toluene Chemical compound CCCCO.CC1=CC=CC=C1 OTXQUGSUXRBUTC-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- ZZXGNRZPAWXART-UHFFFAOYSA-N butoxy(nonyl)phosphinous acid Chemical class CCCCCCCCCP(O)OCCCC ZZXGNRZPAWXART-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- KNQVWTDLQQGKSV-UHFFFAOYSA-O hydroxy-oxo-phenylphosphanium Chemical compound O[P+](=O)C1=CC=CC=C1 KNQVWTDLQQGKSV-UHFFFAOYSA-O 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HTGOEGJIQYGQAG-UHFFFAOYSA-N methyl(3-methylbutoxy)phosphinous acid Chemical compound CC(C)CCOP(C)O HTGOEGJIQYGQAG-UHFFFAOYSA-N 0.000 description 1
- XXYFWGYZXJXNAZ-UHFFFAOYSA-N methyl(pentoxy)phosphinous acid Chemical compound CCCCCOP(C)O XXYFWGYZXJXNAZ-UHFFFAOYSA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NPLLNBVTXXLWKF-UHFFFAOYSA-N nonylphosphonous acid Chemical class CCCCCCCCCP(O)O NPLLNBVTXXLWKF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CGNKSELPNJJTSM-UHFFFAOYSA-N phenylphosphonous acid Chemical compound OP(O)C1=CC=CC=C1 CGNKSELPNJJTSM-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3146197.2 | 1981-11-21 | ||
| DE19813146197 DE3146197A1 (de) | 1981-11-21 | 1981-11-21 | Verfahren zur herstellung von phosphonigsaeuremonoalkylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5892689A JPS5892689A (ja) | 1983-06-02 |
| JPH037677B2 true JPH037677B2 (enExample) | 1991-02-04 |
Family
ID=6146901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57202249A Granted JPS5892689A (ja) | 1981-11-21 | 1982-11-19 | 亜ホスホン酸モノアルキルエステルの製法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4474711A (enExample) |
| EP (1) | EP0081694B1 (enExample) |
| JP (1) | JPS5892689A (enExample) |
| CA (1) | CA1190557A (enExample) |
| DE (2) | DE3146197A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008063627A1 (de) * | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monohydroxyfunktionalisierten Dialkylphosphinsäuren,-estern und -salzen mittels Ethylenoxid und ihre Verwendung |
| CN102351900A (zh) * | 2011-08-18 | 2012-02-15 | 江苏优士化学有限公司 | 一种单烷基次膦酸酯的合成方法 |
| EA036169B1 (ru) | 2014-05-13 | 2020-10-09 | Басф Се | Способ получения фосфорсодержащих циангидринов |
| MX2018002731A (es) | 2015-09-02 | 2018-04-13 | Bayer Cropscience Ag | Proceso para la elaboracion de esteres de cianohidrina que contienen fosforo. |
| KR20180048894A (ko) | 2015-09-02 | 2018-05-10 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 인 함유 시아노하이드린 에스테르의 제조 방법 |
| JP2018526379A (ja) | 2015-09-02 | 2018-09-13 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | リン含有シアノヒドリンエステルの製造方法 |
| BR112018004247A2 (pt) | 2015-09-02 | 2018-09-25 | Bayer Cropscience Aktiengesellschaft | método para produção de ésteres de cianidrina contendo fósforo. |
| JP6826110B2 (ja) | 2015-09-29 | 2021-02-03 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | ホスフィネート類を製造する方法 |
| KR102092131B1 (ko) * | 2016-11-10 | 2020-03-23 | 주식회사 엘지화학 | 비할로겐 난연수지 조성물 |
| TW201840578A (zh) | 2017-02-22 | 2018-11-16 | 以色列商亞當阿甘公司 | 製備甲基膦酸丁基酯的方法 |
| WO2025219238A1 (en) | 2024-04-15 | 2025-10-23 | Basf Se | Process for producing l-glufosinate from a diol or diol derivative |
| WO2025219236A1 (en) | 2024-04-15 | 2025-10-23 | Basf Se | Process for preparing phosphorous containing diols or diol derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU161748A (enExample) * | ||||
| SU172792A (enExample) * | ||||
| US2860155A (en) * | 1956-04-30 | 1958-11-11 | Victor Chemical Works | Phosphinates and methods of preparing same |
| DE1668031C3 (de) * | 1967-10-13 | 1978-03-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dialkylphosphiten |
-
1981
- 1981-11-21 DE DE19813146197 patent/DE3146197A1/de not_active Withdrawn
-
1982
- 1982-11-16 EP EP82110560A patent/EP0081694B1/de not_active Expired
- 1982-11-16 DE DE8282110560T patent/DE3262351D1/de not_active Expired
- 1982-11-19 CA CA000415973A patent/CA1190557A/en not_active Expired
- 1982-11-19 US US06/443,132 patent/US4474711A/en not_active Expired - Lifetime
- 1982-11-19 JP JP57202249A patent/JPS5892689A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1190557A (en) | 1985-07-16 |
| DE3146197A1 (de) | 1983-05-26 |
| EP0081694B1 (de) | 1985-02-13 |
| DE3262351D1 (en) | 1985-03-28 |
| JPS5892689A (ja) | 1983-06-02 |
| US4474711A (en) | 1984-10-02 |
| EP0081694A1 (de) | 1983-06-22 |
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