PL102521B1 - Sposob wytwarzania meta-fenoksybenzaldehydu - Google Patents

Sposob wytwarzania meta-fenoksybenzaldehydu Download PDF

Info

Publication number: PL102521B1
Authority: PL; Poland
Prior art keywords: meta; mixture; halide; phenoxybenzaldehyde; formula
Prior art date: 1976-02-05

Application number

PL1977195774A

Other languages

English (en)

Polish (pl)

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.)

1976-02-05

Filing date

1977-02-03

Publication date

1979-04-30

1977-02-03 Application filed filed Critical

1979-04-30 Publication of PL102521B1 publication Critical patent/PL102521B1/pl

Links

MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title description 7
239000000203 mixture Substances 0.000 claims description 37
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
150000004820 halides Chemical class 0.000 claims description 14
UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 10
229910021529 ammonia Inorganic materials 0.000 claims description 8
239000003999 initiator Substances 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
238000005658 halogenation reaction Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
230000026030 halogenation Effects 0.000 claims description 6
230000008569 process Effects 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000012454 non-polar solvent Substances 0.000 claims description 2
150000002978 peroxides Chemical class 0.000 claims description 2
QERKFICIDPEWPD-UHFFFAOYSA-N 3-methyl-2-phenoxybenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1OC1=CC=CC=C1 QERKFICIDPEWPD-UHFFFAOYSA-N 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
-1 benzyl halide Chemical class 0.000 description 13
230000007062 hydrolysis Effects 0.000 description 11
238000006460 hydrolysis reaction Methods 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
238000005660 chlorination reaction Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
239000002253 acid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000031709 bromination Effects 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
VCJZTATVUDMNLU-UHFFFAOYSA-N dibromomethylbenzene Chemical compound BrC(Br)C1=CC=CC=C1 VCJZTATVUDMNLU-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
150000001649 bromium compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
230000000977 initiatory effect Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000004312 hexamethylene tetramine Substances 0.000 description 2
235000010299 hexamethylene tetramine Nutrition 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229960004011 methenamine Drugs 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical class ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
240000008574 Capsicum frutescens Species 0.000 description 1
239000004215 Carbon black (E152) Substances 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
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
238000006007 Sommelet synthesis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000003749 cleanliness Effects 0.000 description 1
239000003245 coal Substances 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003828 free initiator Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

PL1977195774A 1976-02-05 1977-02-03 Sposob wytwarzania meta-fenoksybenzaldehydu PL102521B1 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4577/76A GB1568380A (en)	1976-02-05	1976-02-05	Preparation of meta-aryloxybenzaldehydes

Publications (1)

Publication Number	Publication Date
PL102521B1 true PL102521B1 (pl)	1979-04-30

Family

ID=9779779

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1977195774A PL102521B1 (pl)	1976-02-05	1977-02-03	Sposob wytwarzania meta-fenoksybenzaldehydu

Country Status (6)

Country	Link
BE (1)	BE851048A (fr)
CU (1)	CU34667A (fr)
GB (1)	GB1568380A (fr)
PL (1)	PL102521B1 (fr)
SU (1)	SU695553A3 (fr)
ZA (1)	ZA77606B (fr)

1976
- 1976-02-05 GB GB4577/76A patent/GB1568380A/en not_active Expired
1977
- 1977-01-31 SU SU772445201A patent/SU695553A3/ru active
- 1977-02-03 ZA ZA770606A patent/ZA77606B/xx unknown
- 1977-02-03 BE BE174626A patent/BE851048A/fr not_active IP Right Cessation
- 1977-02-03 PL PL1977195774A patent/PL102521B1/pl unknown
- 1977-02-03 CU CU7734667A patent/CU34667A/es unknown

Also Published As

Publication number	Publication date
BE851048A (fr)	1977-08-03
CU34667A (es)	1981-04-20
SU695553A3 (ru)	1979-10-30
GB1568380A (en)	1980-05-29
ZA77606B (en)	1977-12-28

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