NO123573B - - Google Patents

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Info

Publication number: NO123573B
Authority: NO; Norway
Prior art keywords: benzene; monochlorobenzene; polychlorobenzenes; phenol; chlorine
Prior art date: 1967-12-30

Application number

NO497168A

Other languages

English (en)

Norwegian (no)

Inventor

H Krekeler

W Riemenschneider

L Hoernig

T Quadflieg

Original Assignee

Hoechst Ag

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.)

1967-12-30

Filing date

1968-12-12

Publication date

1971-12-13

1968-12-12 Application filed by Hoechst Ag filed Critical Hoechst Ag

1971-12-13 Publication of NO123573B publication Critical patent/NO123573B/no

Links

UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 108
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 35
238000000034 method Methods 0.000 claims description 25
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 24
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
230000007062 hydrolysis Effects 0.000 claims description 12
238000006460 hydrolysis reaction Methods 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 7
-1 polyphenylene Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 3
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229920000265 Polyparaphenylene Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229920006389 polyphenyl polymer Chemical class 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
229920013636 polyphenyl ether polymer Chemical class 0.000 claims 1
150000001555 benzenes Chemical class 0.000 description 15
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 11
239000006227 byproduct Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
229940117389 dichlorobenzene Drugs 0.000 description 10
238000000926 separation method Methods 0.000 description 7
GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
230000007306 turnover Effects 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
235000010290 biphenyl Nutrition 0.000 description 3
125000006267 biphenyl group Chemical class 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000008442 polyphenolic compounds Chemical class 0.000 description 2
235000013824 polyphenols Nutrition 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 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
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
WGKMWBIFNQLOKM-UHFFFAOYSA-N [O].[Cl] Chemical compound [O].[Cl] WGKMWBIFNQLOKM-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000012084 conversion product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
238000007700 distillative separation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
- C07C19/03—Chloromethanes
- C07C19/041—Carbon tetrachloride

Landscapes

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

NO497168A 1967-12-30 1968-12-12 NO123573B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0054449		1967-12-30

Publications (1)

Publication Number	Publication Date
NO123573B true NO123573B (de)	1971-12-13

Family

ID=7107094

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO497168A NO123573B (de)	1967-12-30	1968-12-12

Country Status (5)

Country	Link
AT (1)	AT293347B (de)
BE (1)	BE726257A (de)
DE (1)	DE1643386A1 (de)
NL (1)	NL6818525A (de)
NO (1)	NO123573B (de)

1967
- 1967-12-30 DE DE19671643386 patent/DE1643386A1/de active Pending
1968
- 1968-12-12 NO NO497168A patent/NO123573B/no unknown
- 1968-12-23 NL NL6818525A patent/NL6818525A/xx unknown
- 1968-12-27 AT AT1260968A patent/AT293347B/de not_active IP Right Cessation
- 1968-12-30 BE BE726257D patent/BE726257A/xx unknown

Also Published As

Publication number	Publication date
AT293347B (de)	1971-10-11
NL6818525A (de)	1969-07-02
DE1643386A1 (de)	1971-07-08
BE726257A (de)	1969-05-29

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