CA1197260A - Preparation d'esters allyliques de l'acide tetrabromophtalique - Google Patents

Preparation d'esters allyliques de l'acide tetrabromophtalique

Info

Publication number: CA1197260A
Authority: CA; Canada
Prior art keywords: allylic; alcohol; solution; tetrabromophthalic; allyl
Prior art date: 1982-11-23
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

Application number

CA000416147A

Other languages

English (en)

Inventor

Joseph H. Finley

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FMC Corp

Original Assignee

FMC Corp

Priority date (The priority date 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 date listed.)

1982-11-23

Filing date

1982-11-23

Publication date

1985-11-26

1982-11-23 Application filed by FMC Corp filed Critical FMC Corp

1982-11-23 Priority to CA000416147A priority Critical patent/CA1197260A/fr

1985-11-26 Application granted granted Critical

1985-11-26 Publication of CA1197260A publication Critical patent/CA1197260A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 36
XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 title claims abstract description 17
125000000746 allylic group Chemical group 0.000 title claims abstract description 8
230000008569 process Effects 0.000 title abstract description 11
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 108
239000002904 solvent Substances 0.000 claims abstract description 22
QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 claims abstract description 16
-1 allylic halide Chemical class 0.000 claims abstract description 15
150000005690 diesters Chemical class 0.000 claims abstract description 13
150000002148 esters Chemical class 0.000 claims abstract description 9
239000000376 reactant Substances 0.000 claims abstract description 9
239000002994 raw material Substances 0.000 claims abstract description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
239000000243 solution Substances 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 21
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical group ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 12
229940086542 triethylamine Drugs 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
230000003197 catalytic effect Effects 0.000 claims description 8
GATVZVWABXPTPF-UHFFFAOYSA-M triethyl(prop-2-enyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC=C GATVZVWABXPTPF-UHFFFAOYSA-M 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 6
150000003512 tertiary amines Chemical class 0.000 claims description 6
238000004821 distillation Methods 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
VZNSVWKHKHDGCM-UHFFFAOYSA-N 3,3,4,4,4-pentafluoro-2-methylbutan-2-ol Chemical compound CC(C)(O)C(F)(F)C(F)(F)F VZNSVWKHKHDGCM-UHFFFAOYSA-N 0.000 claims description 3
BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 claims description 2
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical group CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
238000003556 assay Methods 0.000 description 12
239000002253 acid Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000004641 Diallyl-phthalate Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
229940083608 sodium hydroxide Drugs 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
238000005406 washing Methods 0.000 description 4
DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
239000012046 mixed solvent Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
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 2
FZAZPMLWYUKRAE-UHFFFAOYSA-N 2,4,6-trinitrobenzene-1,3-diamine Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(N)=C1[N+]([O-])=O FZAZPMLWYUKRAE-UHFFFAOYSA-N 0.000 description 2
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
230000032050 esterification Effects 0.000 description 2
239000003063 flame retardant Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229960005419 nitrogen Drugs 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000036647 reaction Effects 0.000 description 2
238000004064 recycling Methods 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
101000588145 Homo sapiens Microtubule-associated tumor suppressor 1 Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
102100031550 Microtubule-associated tumor suppressor 1 Human genes 0.000 description 1
102100029290 Transthyretin Human genes 0.000 description 1
108050000089 Transthyretin Proteins 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
UABBDCURCBTIIQ-UHFFFAOYSA-N bis(prop-2-enyl) 3,4,5,6-tetrachlorobenzene-1,2-dicarboxylate Chemical compound ClC1=C(Cl)C(Cl)=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1Cl UABBDCURCBTIIQ-UHFFFAOYSA-N 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
UTNQAECQSKUEGD-UHFFFAOYSA-L disodium;3,4,5,6-tetrabromophthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C([O-])=O UTNQAECQSKUEGD-UHFFFAOYSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
BWBONKHPVHMQHE-UHFFFAOYSA-N tiocarlide Chemical compound C1=CC(OCCC(C)C)=CC=C1NC(=S)NC1=CC=C(OCCC(C)C)C=C1 BWBONKHPVHMQHE-UHFFFAOYSA-N 0.000 description 1
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000416147A 1982-11-23 1982-11-23 Preparation d'esters allyliques de l'acide tetrabromophtalique Expired CA1197260A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000416147A CA1197260A (fr)	1982-11-23	1982-11-23	Preparation d'esters allyliques de l'acide tetrabromophtalique

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000416147A CA1197260A (fr)	1982-11-23	1982-11-23	Preparation d'esters allyliques de l'acide tetrabromophtalique

Publications (1)

Publication Number	Publication Date
CA1197260A true CA1197260A (fr)	1985-11-26

Family

ID=4123997

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000416147A Expired CA1197260A (fr)	1982-11-23	1982-11-23	Preparation d'esters allyliques de l'acide tetrabromophtalique

Country Status (1)

Country	Link
CA (1)	CA1197260A (fr)

1982
- 1982-11-23 CA CA000416147A patent/CA1197260A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-11-26	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20021126

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