DE1242228B - Process for the production of halogen-containing organic phosphonates - Google Patents
Process for the production of halogen-containing organic phosphonatesInfo
- Publication number
- DE1242228B DE1242228B DEP32970A DEP0032970A DE1242228B DE 1242228 B DE1242228 B DE 1242228B DE P32970 A DEP32970 A DE P32970A DE P0032970 A DEP0032970 A DE P0032970A DE 1242228 B DE1242228 B DE 1242228B
- Authority
- DE
- Germany
- Prior art keywords
- tris
- phosphite
- glycol
- halogen
- production
- 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229910052736 halogen Inorganic materials 0.000 title claims description 3
- 150000002367 halogens Chemical class 0.000 title claims description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 chloropropoxy-isopropyl Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 125000004437 phosphorous atom Chemical group 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000004953 trihalomethyl group Chemical group 0.000 description 3
- PMIGJHGQHKWNMH-UHFFFAOYSA-N P(O)(O)=O.ClC(Cl)Cl Chemical compound P(O)(O)=O.ClC(Cl)Cl PMIGJHGQHKWNMH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- KKRYTWVAKLKNFI-UHFFFAOYSA-N 2-hydroxyethyl dihydrogen phosphite Chemical compound OCCOP(O)O KKRYTWVAKLKNFI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BJXXCOMGRRCAGN-CLFAGFIQSA-N [2,2-bis(hydroxymethyl)-3-[(z)-octadec-9-enoyl]oxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCC\C=C/CCCCCCCC BJXXCOMGRRCAGN-CLFAGFIQSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002023 wood Substances 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/388—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5078—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to hydrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Fireproofing Substances (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. α.:Int. α .:
C07fC07f
Deutsche KI.: 12 ο-26/01German KI .: 12 ο-26/01
Nummer: 1242Number: 1242
Aktenzeichen: P 32970IV b/12 οFile number: P 32970IV b / 12 ο
Anmeldetag: 13. November 1963Filing date: November 13, 1963
Auslegetag: 15. Juni 1967Open date: June 15, 1967
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung halogenhaltiger organischer Phosphonate.The invention relates to a process for the production of halogen-containing organic phosphonates.
Erfindungsgemäß erhält man die Phosphonate dadurch, daß man ein Tris-polyalkylenglykol-phosphit oder eine Verbindung der allgemeinen FormelAccording to the invention, the phosphonates are obtained by using a tris-polyalkylene glycol phosphite or a compound of the general formula
Ri-ORi-O
R?
O
OR3OP-R?
O
OR 3 OP
OR5 OR 5
OR4OPOR 4 OP
R2-O v ' OR6 R 2 -O v ' OR 6
in der Ri, R2, R5, R6 und R7 Reste von Polyalkylenglykolen sind, denen eine Hydroxylgruppe fehlt, Rs und R.J Reste von Polyalkylenglykolen, denen beide Hydroxylgruppen fehlen und η Null oder eine ganze Zahl ist, mit einer1 Verbindung der allgemeinen Formelin which Ri, R2, R5, R6 and R7 are residues of polyalkylene glycols which lack one hydroxyl group, Rs and RJ are residues of polyalkylene glycols which both lack hydroxyl groups and η is zero or an integer, with a 1 compound of the general formula
γγ
■Ä1■ Ä1
in der Xi, X2, X3 und X4 Chlor oder Brom bedeuten,in which Xi, X2, X3 and X 4 are chlorine or bromine,
Verfahren zur Herstellung halogenhaltiger organischer PhosphonateProcess for the production of halogenated organic phosphonates
Anmelder:Applicant:
Pure Chemicals Limited, Liverpool (Großbritannien)Pure Chemicals Limited, Liverpool (Great Britain)
Vertreter:Representative:
Dipl.-Chem. W. Rücker, Patentanwalt, Hannover, Am Klagesmarkt 10-11Dipl.-Chem. W. Rücker, patent attorney, Hanover, Am Klagesmarkt 10-11
Als Erfinder benannt: Lester Friedman, Beachwood, Ohio (V. St. A.)Named inventor: Lester Friedman, Beachwood, Ohio (V. St. A.)
Xi darüber hinaus auch für Wasserstoff stehen kann, in an sich bekannter Weise umsetzt.Xi can also stand for hydrogen, in a manner known per se.
Vorzugsweise wird die Umsetzung mit Tetrachlorkohlenstoff durchgeführt. Es können aber auch beispielsweise Kohlenstofftetrabromid, Chloroform oder Bromoform eingesetzt werden.The reaction is preferably carried out with carbon tetrachloride. But it can also for example carbon tetrabromide, chloroform or bromoform can be used.
Die erfindungsgemäß hergestellten Phosphonate haben entweder die FormelThe phosphonates prepared according to the invention either have the formula
/ \
/
/yOP -
/ y
\ t OR 3 OP
\ t
\ / OR 4 OP
\ /
IlIl
RiOPRiOP
R7 \ OR 7 \ O
OR3OP-OR 3 OP
(ID(ID
OR1OPOR 1 OP
X2-CX 2 -C
RiOP — OR3OP — OR4OP oder / \ ln RiOP - OR 3 OP - OR 4 OP or / \ ln
//Xi// Xi
OR5 OR 5
OR6 OR 6
C-X2 CX 2
/Xl/ Xl
C-X2 CX 2
vc—X2 "^x3 v c-X 2 "^ x 3
(IV)(IV)
in denen Ri, R3 bis R7, Xi, Xo, X3 und η die obige gruppen sind und m eine ganze Zahl von wenig-Bedeutung haben und R8, Rg, Rio und Rn Alkylen- stens 1 bedeutet.in which Ri, R 3 to R 7 , Xi, Xo, X 3 and η are the above groups and m have an integer of little significance and R 8 , Rg, Rio and Rn denote at least 1 alkylene.
709 590/350709 590/350
Falls nur ein Phosphoratom in dem Ausgangsmolekül vorhanden ist, bildet sich selbst beim Überschuß von Kohlenstofftetrahalogenid oder Haloform nur eine Phosphonatgruppe. Falls mehr als ein Phosphoratom vorhanden ist, bildet sich bei äquimolaren Mengen von Phosphit und Kohlenstofftetrahalogenid oder Haloform ein Monophosphonat. Ist jedoch ein Überschuß an Kohlenstofftetrahalogenid oder Haloform verwendet worden, werden mehr als eine Phosphitgruppe zu einer Phosphonatgruppe umgewandelt, so daß sich die Produkte der Formeln III und IV bilden.If there is only one phosphorus atom in the parent molecule, it will form even if it is in excess of carbon tetrahalide or haloform only one phosphonate group. If more than one Phosphorus atom is present, is formed with equimolar amounts of phosphite and carbon tetrahalide or haloform a monophosphonate. However, it is an excess of carbon tetrahalide or haloform has been used, more than one phosphite group becomes a phosphonate group converted so that the products of formulas III and IV are formed.
Die Phosphonate der Erfindung besitzen wertvolle Eigenschaften, beispielsweise feuerhemmende oder verbrennungshemmende Eigenschaften und können in Kunststoffen, beispielsweise Polyestern und Polyurethanen, zur Beschichtung von Textilien, Holz, Glas oder Stahl, zur Isolation, als Verpackungsmittel usw. verwandt werden.The phosphonates of the invention have valuable properties, for example fire retardant or combustion-retardant properties and can be found in plastics such as polyesters and polyurethanes, for coating textiles, wood, glass or steel, for insulation, as packaging material etc. can be used.
Da die Trihalogenmethylgruppe direkt mit dem Phosphoratom verbunden ist und zwischen der Trihalogenmethylgruppe und dem Phosphoratom keine Methylgruppe liegt, ergibt sich der Vorteil, daß bei den erfindungsgemäßen Verbindungen kein Halogenwasserstoff, z. B. Chlorwasserstoff, abgespalten wird wie bei den anderen Verbindungen, bei denen die Trihalogenmethylgruppe über eine Methylengruppe an das Phosphoratom gebunden ist.Since the trihalomethyl group is connected directly to the phosphorus atom and between the Trihalomethyl group and the phosphorus atom is not a methyl group, there is an advantage that in the compounds according to the invention no hydrogen halide, e.g. B. hydrogen chloride, split off is as with the other compounds in which the trihalomethyl group has a methylene group is bound to the phosphorus atom.
Als Ausgangspolyalkylenglykolphosphite können verwendet werden: Tris-dipropylenglykol-phosphit, Tris-tripropylenglykol-phosphit, Tris-polypropylenglykol - 425 - phosphit, Tris - polypropylenglykol-3000-phosphit, Tris-polypropylenglykol- 1025-phosphit, Tris-polypropylengIykol-2025-phosphit, Trisdiäthylenglykol-phosphit, Tris-triäthylenglykol-phosphit und Tris-polyäthylenglykol-2000-phosphit und Tris-ditetramethylenglykol-phosphit.The following can be used as starting polyalkylene glycol phosphites: tris-dipropylene glycol phosphite, Tris-tripropylene glycol phosphite, tris-polypropylene glycol - 425 - phosphite, Tris - polypropylene glycol 3000 phosphite, Tris polypropylene glycol 1025 phosphite, Tris-polypropylene glycol-2025-phosphite, tris-diethylene glycol-phosphite, Tris-triethylene glycol-phosphite and tris-polyethylene glycol-2000-phosphite and Tris-ditetramethylene glycol phosphite.
Von den Ausgangsphosphiten gemäß der oben angegebenen allgemeinen Formel können verwendet werden: Dipropylenglykol-tetrol-diphosphit, Dipropylenglykol - pentol - triphosphit, Tripropylenglykoltetrol-diphosphit, Polypropylenglykol-425-tetroI-diphosphit, Diäthylenglykol - tetrol - diphosphit, Diäthylenglykol-pentol-triphosphit und Ditetramethylenglykol-tetrol-diphosphit. Of the starting phosphites according to the general formula given above, can be used be: dipropylene glycol tetrol diphosphite, dipropylene glycol - pentol - triphosphite, tripropylene glycol tetrol diphosphite, polypropylene glycol 425 tetroI diphosphite, Diethylene glycol - tetrol - diphosphite, diethylene glycol pentol triphosphite and ditetramethylene glycol tetrol diphosphite.
Da es schwierig ist, nichtflüchtige Nebenprodukte Ri — OSince it is difficult to remove non-volatile by-products Ri - O
abzutrennen, wenn hochmolekulare Phosphite verwendet werden, sind die bevorzugten Ausgangsverbindungen Tris-dipropylenglykol-phosphit, Tris-di- / äthylenglykol-phosphit, Dipropylenglykol-tetrol-di-50 R2— O phosphit und Dipropylenglykol-pentol-triphosphit. Die Produkte der Polypropylenglykol-phosphite haben häufig eine bessere Stabilität als die Produkte der Polyäthylenglykol-phosphite und werden daher bevorzugt. 55separated when high molecular weight phosphites are used are the preferred starting compounds Tris-dipropylene glycol-phosphite, tris-di- / ethylene glycol-phosphite, dipropylene glycol-tetrol-di-50 R2-0 phosphite and dipropylene glycol pentole triphosphite. The products of polypropylene glycol phosphites often have a better stability than the products of polyethylene glycol phosphites and are therefore preferred. 55
Die angegebenen Prozentsätze und Teile sind Gewichtsprozente und Gewichtsteile, falls nichts anderes vermerkt ist.The percentages and parts given are percentages by weight and parts by weight, if nothing other is noted.
kuum abgetrennt. Die zurückbleibende Flüssigkeit ist Bis-dipropylenglykol-trichlormethan-phosphonat. Molekulargewicht: 431; Phosphorgehalt: 7,2°/q.kuum separated. The remaining liquid is bis-dipropylene glycol trichloromethane phosphonate. Molecular Weight: 431; Phosphorus content: 7.2% / q.
Das Verfahren gemäß Beispiel 1 wird mit 0,2 Mol Tris-diäthylenglykol-phosphit statt Tris-dipropylenglykol-phosphit wiederholt, so daß als flüssiger Rückstand nach der Entfernung der flüchtigen Bestandteile Bis-diäthylenglykol-trichlormethan-phosphonat verbleibt mit einem Molekulargewicht von 375 und einem Phosphorgehalt von 8,2%.The process according to Example 1 is carried out with 0.2 mol of tris-diethylene glycol phosphite instead of tris-dipropylene glycol phosphite repeated so that as a liquid residue after removal of the volatile constituents Bis-diethylene glycol trichloromethane phosphonate remains with a molecular weight of 375 and a phosphorus content of 8.2%.
Das Verfahren nach Beispiel 1 wird mit 500 ml Kohlenstofftetrabromid statt Kohlenstofftetrachlorid wiederholt, und als flüssiger Rückstand bleibt Dipropylenglykol-tribrommethan-phosphonat mit einem Molekulargewicht von 565 und einem Phosphorgehalt von 5,5°/o.The method according to Example 1 is carried out with 500 ml of carbon tetrabromide instead of carbon tetrachloride repeatedly, and dipropylene glycol tribromomethane phosphonate remains as a liquid residue with a molecular weight of 565 and a phosphorus content of 5.5%.
Das Verfahren nach Beispiel 1 wird mit 500 ml Chloroform statt Kohlenstofftetrachlorid durchgeführt und ergibt Dipropylenglykol-dichlormethanphosphonat als flüssigen Rückstand. Molekulargewicht: 397; Phosphorgehalt: 7,8%.The method according to Example 1 is carried out with 500 ml of chloroform instead of carbon tetrachloride and gives dipropylene glycol dichloromethane phosphonate as a liquid residue. Molecular weight: 397; Phosphorus content: 7.8%.
Das Verfahren nach Beispiel 1 wird mit 0,2 Mol Dipropylenglykol-tetrol-diphosphit statt Tris-dipropylenglykol-phosphit durchgeführt, so daß sich als flüssiger Rückstand Dipropylenglykol-diol-bis-(trichlormethan - diphosphonat) ergibt. Molekulargewicht: 729; Phosphorgehalt: 8,5%.The method according to Example 1 is carried out with 0.2 mol of dipropylene glycol tetrol diphosphite instead of tris-dipropylene glycol phosphite, so that liquid residue results in dipropylene glycol diol bis (trichloromethane - diphosphonate). Molecular weight: 729; Phosphorus content: 8.5%.
Claims (2)
OR3OP—O
OR 3 OP—
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4258363A GB1012630A (en) | 1963-10-29 | 1963-10-29 | Halogen-containing phosphonates and polyurethanes |
| DEP32970A DE1242228B (en) | 1963-10-29 | 1963-11-13 | Process for the production of halogen-containing organic phosphonates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4258363A GB1012630A (en) | 1963-10-29 | 1963-10-29 | Halogen-containing phosphonates and polyurethanes |
| DEP32970A DE1242228B (en) | 1963-10-29 | 1963-11-13 | Process for the production of halogen-containing organic phosphonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1242228B true DE1242228B (en) | 1967-06-15 |
Family
ID=41718988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP32970A Pending DE1242228B (en) | 1963-10-29 | 1963-11-13 | Process for the production of halogen-containing organic phosphonates |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1242228B (en) |
| GB (1) | GB1012630A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE845226C (en) * | 1948-05-10 | 1952-07-31 | Bataafsche Petroleum | lubricant |
| FR1216521A (en) * | 1958-11-28 | 1960-04-26 | Omnium De Prod Chim Pour L Ind | Polyphosphonic esters |
-
1963
- 1963-10-29 GB GB4258363A patent/GB1012630A/en not_active Expired
- 1963-11-13 DE DEP32970A patent/DE1242228B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE845226C (en) * | 1948-05-10 | 1952-07-31 | Bataafsche Petroleum | lubricant |
| FR1216521A (en) * | 1958-11-28 | 1960-04-26 | Omnium De Prod Chim Pour L Ind | Polyphosphonic esters |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1012630A (en) | 1965-12-08 |
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