BE604373A - - Google Patents
Info
- Publication number
- BE604373A BE604373A BE604373DA BE604373A BE 604373 A BE604373 A BE 604373A BE 604373D A BE604373D A BE 604373DA BE 604373 A BE604373 A BE 604373A
- Authority
- BE
- Belgium
- Prior art keywords
- chloro
- acid
- phosphorus
- formula
- compounds
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 239000011574 phosphorus Substances 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000003018 phosphorus compounds Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 14
- 235000011007 phosphoric acid Nutrition 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- -1 2,5-dichloro-5,4-epoxyhexan Chemical compound 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003017 phosphorus Chemical class 0.000 description 3
- SKCLYNFYASNQIL-UHFFFAOYSA-N 2-(chloromethyl)-2-ethyl-3-propyloxirane Chemical compound CCCC1OC1(CC)CCl SKCLYNFYASNQIL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LECYALNHBVILEC-UHFFFAOYSA-N 2,3-bis(1-chlorobutyl)oxirane Chemical compound CCCC(Cl)C1OC1C(Cl)CCC LECYALNHBVILEC-UHFFFAOYSA-N 0.000 description 1
- VUSYFNXNYLAECV-UHFFFAOYSA-N 2,3-bis(chloromethyl)oxirane Chemical compound ClCC1OC1CCl VUSYFNXNYLAECV-UHFFFAOYSA-N 0.000 description 1
- UKXROSORAUTSSH-UHFFFAOYSA-N 2-(1,2-dichloroethyl)oxirane Chemical compound ClCC(Cl)C1CO1 UKXROSORAUTSSH-UHFFFAOYSA-N 0.000 description 1
- STDUFFCKPIBQPO-UHFFFAOYSA-N 2-(1-chlorobutyl)-3-ethyloxirane Chemical compound ClC(C1C(CC)O1)CCC STDUFFCKPIBQPO-UHFFFAOYSA-N 0.000 description 1
- RVWYSKJXNJEXQE-UHFFFAOYSA-N 2-(1-chloroethyl)-3-(1-chlorohexyl)oxirane Chemical compound ClC(C)C1C(C(CCCCC)Cl)O1 RVWYSKJXNJEXQE-UHFFFAOYSA-N 0.000 description 1
- LVZPWXWJBDPQNI-UHFFFAOYSA-N 2-(1-chloroethyl)-3-(1-chloropropyl)oxirane Chemical compound ClC(C)C1C(C(CC)Cl)O1 LVZPWXWJBDPQNI-UHFFFAOYSA-N 0.000 description 1
- OLCJJGKCAJKPJT-UHFFFAOYSA-N 2-(1-chloroethyl)-3-(chloromethyl)oxirane Chemical compound CC(Cl)C1OC1CCl OLCJJGKCAJKPJT-UHFFFAOYSA-N 0.000 description 1
- ZPENLTGGQAFXHN-UHFFFAOYSA-N 2-(1-chloroethyl)-3-methyloxirane Chemical compound CC(Cl)C1OC1C ZPENLTGGQAFXHN-UHFFFAOYSA-N 0.000 description 1
- VPCIBEXVZVMHNG-UHFFFAOYSA-N 2-(1-chloroethyl)-3-pentyloxirane Chemical compound ClC(C)C1C(CCCCC)O1 VPCIBEXVZVMHNG-UHFFFAOYSA-N 0.000 description 1
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 1
- JSAPJQPHCHLOPE-UHFFFAOYSA-N 2-(1-chloropentyl)-3-methyloxirane Chemical compound ClC(C1C(C)O1)CCCC JSAPJQPHCHLOPE-UHFFFAOYSA-N 0.000 description 1
- PNAYHDVCJCAJME-UHFFFAOYSA-N 2-(chloromethyl)-3-ethyloxirane Chemical compound CCC1OC1CCl PNAYHDVCJCAJME-UHFFFAOYSA-N 0.000 description 1
- JOJOMYICHZJKLN-UHFFFAOYSA-N 2-(chloromethyl)-3-heptyloxirane Chemical compound CCCCCCCC1OC1CCl JOJOMYICHZJKLN-UHFFFAOYSA-N 0.000 description 1
- COHPEBVGRVKJKY-UHFFFAOYSA-N 2-butyl-3-(1-chlorobutyl)oxirane Chemical compound ClC(CCC)C1C(CCCC)O1 COHPEBVGRVKJKY-UHFFFAOYSA-N 0.000 description 1
- XXCXJRVAQQMPLN-UHFFFAOYSA-N 2-butyl-3-(1-chloropropyl)oxirane Chemical compound CCCCC1OC1C(Cl)CC XXCXJRVAQQMPLN-UHFFFAOYSA-N 0.000 description 1
- MMJGNKUFFPODNG-UHFFFAOYSA-N 2-butyl-3-(chloromethyl)oxirane Chemical compound CCCCC1OC1CCl MMJGNKUFFPODNG-UHFFFAOYSA-N 0.000 description 1
- QKHUXWLXTLMABH-UHFFFAOYSA-N 2-butyl-3-ethyloxirane Chemical compound CCCCC1OC1CC QKHUXWLXTLMABH-UHFFFAOYSA-N 0.000 description 1
- JBUKNEPAIIKSPM-UHFFFAOYSA-N 2-ethyl-3-hexyloxirane Chemical compound CCCCCCC1OC1CC JBUKNEPAIIKSPM-UHFFFAOYSA-N 0.000 description 1
- GSTZVCRHAKCHCF-UHFFFAOYSA-N 2-heptyl-3-methyloxirane Chemical compound CCCCCCCC1OC1C GSTZVCRHAKCHCF-UHFFFAOYSA-N 0.000 description 1
- LIESJAYIOKBLIL-UHFFFAOYSA-N 2-methyl-3-propyloxirane Chemical compound CCCC1OC1C LIESJAYIOKBLIL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- QXCXKXNWODTYFX-UHFFFAOYSA-N ClC(C)C1C(CCCCCC)O1 Chemical compound ClC(C)C1C(CCCCCC)O1 QXCXKXNWODTYFX-UHFFFAOYSA-N 0.000 description 1
- JQESLVHQYLWCGN-UHFFFAOYSA-N ClC(C1C(C)O1)CCC Chemical compound ClC(C1C(C)O1)CCC JQESLVHQYLWCGN-UHFFFAOYSA-N 0.000 description 1
- AHAQERCMXHPIRR-UHFFFAOYSA-N ClC(C1C(CCC)O1)CCCC Chemical compound ClC(C1C(CCC)O1)CCCC AHAQERCMXHPIRR-UHFFFAOYSA-N 0.000 description 1
- OQJZONJARLODSA-UHFFFAOYSA-N ClC(CC)C1C(C(CCCC)Cl)O1 Chemical compound ClC(CC)C1C(C(CCCC)Cl)O1 OQJZONJARLODSA-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 244000182067 Fraxinus ornus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000003254 gasoline additive Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005303 weighing Methods 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
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with 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)
- Epoxy Resins (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE604373A true BE604373A (nl) |
Family
ID=192748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE604373D BE604373A (nl) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE604373A (nl) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2036592A1 (de) | 1970-07-23 | 1972-01-27 | Knapsack Ag | Schwer entflammbare Polyurethane sowie Verfahren zu deren Herstellung |
| DE2066183C2 (de) * | 1970-07-23 | 1983-12-08 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung schwer entflammbarer Polyurethane |
-
0
- BE BE604373D patent/BE604373A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2036592A1 (de) | 1970-07-23 | 1972-01-27 | Knapsack Ag | Schwer entflammbare Polyurethane sowie Verfahren zu deren Herstellung |
| DE2066183C2 (de) * | 1970-07-23 | 1983-12-08 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung schwer entflammbarer Polyurethane |
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