DE1234198B - Verfahren zur Herstellung von Trialkylphosphiten - Google Patents
Verfahren zur Herstellung von TrialkylphosphitenInfo
- Publication number
- DE1234198B DE1234198B DES89256A DES0089256A DE1234198B DE 1234198 B DE1234198 B DE 1234198B DE S89256 A DES89256 A DE S89256A DE S0089256 A DES0089256 A DE S0089256A DE 1234198 B DE1234198 B DE 1234198B
- Authority
- DE
- Germany
- Prior art keywords
- phosphite
- reaction
- phase
- trialkyl
- solvent
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 150000003512 tertiary amines Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- -1 phosphorus halide Chemical class 0.000 description 20
- 229910000039 hydrogen halide Inorganic materials 0.000 description 10
- 239000012433 hydrogen halide Substances 0.000 description 10
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US255090A US3235629A (en) | 1963-01-30 | 1963-01-30 | Selective trialkylphosphite extraction process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1234198B true DE1234198B (de) | 1967-02-16 |
Family
ID=22966795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES89256A Pending DE1234198B (de) | 1963-01-30 | 1964-01-28 | Verfahren zur Herstellung von Trialkylphosphiten |
Country Status (7)
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1104616A (fr) * | 1953-10-19 | 1955-11-22 | Monsanto Chemicals | Procédé perfectionné de production d'esters du phosphore |
| US2859238A (en) * | 1956-05-28 | 1958-11-04 | Monsanto Chemicals | Trialkyl phosphites |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB480940A (en) * | 1936-10-10 | 1938-03-02 | Bataafsche Petroleum | A process for preparing pure or substantially pure salts of acid esters of polybasic inorganic acids |
| US2624750A (en) * | 1948-01-23 | 1953-01-06 | Columbia Southern Chem Corp | Process of producing phosphate ester |
| US2658909A (en) * | 1951-09-11 | 1953-11-10 | Howard W Crandall | Process for separation and purification of alkyl phosphoric acids |
| DE1050746B (de) * | 1956-07-06 | 1959-02-19 | Ciba Aktiengesellschaft, Basel (Schweiz) | Verfahren zur Herstellung von Trialkylphosphiten |
| US3068267A (en) * | 1960-06-27 | 1962-12-11 | Stauffer Chemical Co | Process for producing trialkyl phosphites |
| NL274078A (US20110232667A1-20110929-C00004.png) * | 1961-01-31 |
-
1963
- 1963-01-30 US US255090A patent/US3235629A/en not_active Expired - Lifetime
-
1964
- 1964-01-28 DE DES89256A patent/DE1234198B/de active Pending
- 1964-01-28 CH CH100164A patent/CH451896A/de unknown
- 1964-01-28 BE BE643056D patent/BE643056A/xx unknown
- 1964-01-28 DK DK42364AA patent/DK117218B/da unknown
- 1964-01-28 GB GB3678/64A patent/GB1001177A/en not_active Expired
- 1964-01-30 NL NL6400736A patent/NL6400736A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1104616A (fr) * | 1953-10-19 | 1955-11-22 | Monsanto Chemicals | Procédé perfectionné de production d'esters du phosphore |
| US2859238A (en) * | 1956-05-28 | 1958-11-04 | Monsanto Chemicals | Trialkyl phosphites |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6400736A (US20110232667A1-20110929-C00004.png) | 1964-07-31 |
| BE643056A (US20110232667A1-20110929-C00004.png) | 1964-07-28 |
| GB1001177A (en) | 1965-08-11 |
| DK117218B (da) | 1970-03-31 |
| US3235629A (en) | 1966-02-15 |
| CH451896A (de) | 1968-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1230206A2 (de) | Verfahren zur herstellung von ameisensäure | |
| EP0293753A2 (de) | Verfahren zur Herstellung von E-2-Propyl-2-pentensäure und physiologisch verträglichen Salzen derselben | |
| DE1234198B (de) | Verfahren zur Herstellung von Trialkylphosphiten | |
| DE2125587A1 (de) | Verfahren zur Herstellung von Hypophosphiten | |
| DE1261507B (de) | Verfahren zur Gewinnung von Trialkylphosphinen aus einem Reaktionsgemisch | |
| DE1229516B (de) | Verfahren zur Trennung von Alkohol-Alkylcinylaethergemischen | |
| DE1618502A1 (de) | Verfahren zur Herstellung von Polyenverbindungen | |
| DE2111196A1 (de) | Verfahren zur Gewinnung von Adipinsaeure | |
| DE2350851A1 (de) | Verfahren zur herstellung von aliphatischen phosphorsaeuremonoestern | |
| DE965230C (de) | Verfahren zur Wiedergewinnung von Katalysatoren und Nebenprodukten aus den Mutterlaugen der Adipinsaeuregewinnung | |
| DE2425966C2 (de) | Kristallines Natriumsalz der 6-(1-Aminocyclohexan-carboxamido)-penicillansäure, Verfahren zu seiner Herstellung und Arzneimittel, das diese Verbindung enthält | |
| EP0037016B1 (de) | Verfahren zur Extraktion und Gewinnung von Thioglycolsäure aus wässrigen Medien | |
| EP0074591B1 (de) | Verfahren zur Isolierung von Dihydroxybenzol-Monoethern aus Reaktionsgemischen | |
| DE898893C (de) | Verfahren zur Abtrennung aliphatischer Alkohole aus Produkten der katalytischen Kohlenoxydhydrierung | |
| DE1050747B (de) | Verfahren zur Herstellung von Triestern der phosphorigen Säure | |
| DE1418334B1 (de) | Verfahren zur Herstellung von 1,2,3,4,7,7-Hexachlorbicyclo[2,2,1]-2,5-heptadien aus Hexachlorcyclopentadien und Acetylen | |
| DE549110C (de) | Verfahren zur Darstellung von Sterinen, insbesondere Ergosterin, aus Hefe und anderen Pilzen | |
| DE360527C (de) | Verfahren zur Darstellung von Diaethylsulfat | |
| DE857953C (de) | Verfahren zur Herstellung von ª†-Ketopimelinsaeureestern | |
| DE971238C (de) | Verfahren zur Zerlegung von Gemischen sauerstoffhaltiger organischer Verbindungen aus der Kohlenoxydhydrierung und Oxosynthese | |
| DE1259868B (de) | Verfahren zur Herstellung von Milchsaeure | |
| DE619348C (de) | Verfahren zur Herstellung von reinem Diacetyl aus Holzessig oder anderen Diacetyl enthaltenden Gemischen | |
| DE2120248A1 (US20110232667A1-20110929-C00004.png) | ||
| DE1643377A1 (de) | Verfahren zum Treinnen von Fettalkohol-Fettamin-Gemischen | |
| DE1543556C (de) | Verfahren zur Herstellung tertiärer Amme |
