CH619913A5 - Process for the preparation of 2,5-dichloro-p-xylene. - Google Patents

Process for the preparation of 2,5-dichloro-p-xylene. Download PDF

Info

Publication number: CH619913A5
Authority: CH; Switzerland
Prior art keywords: xylene; dichloro; reaction; catalyst; chlorine
Prior art date: 1975-02-04

Application number

CH133376A

Other languages

German (de)

English (en)

Inventor

Samuel Gelfand

Original Assignee

Hooker Chemicals Plastics 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.)

1975-02-04

Filing date

1976-02-03

Publication date

1980-10-31

1976-02-03 Application filed by Hooker Chemicals Plastics Corp filed Critical Hooker Chemicals Plastics Corp

1980-10-31 Publication of CH619913A5 publication Critical patent/CH619913A5/de

Links

238000000034 method Methods 0.000 title claims description 34
UTGSRNVBAFCOEU-UHFFFAOYSA-N 1,4-dichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C=C1Cl UTGSRNVBAFCOEU-UHFFFAOYSA-N 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 3
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 48
239000002904 solvent Substances 0.000 claims description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
239000003054 catalyst Substances 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
239000007795 chemical reaction product Substances 0.000 claims description 10
239000012043 crude product Substances 0.000 claims description 8
229910052959 stibnite Inorganic materials 0.000 claims description 5
MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical class [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 claims description 4
YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical class [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims 1
230000008025 crystallization Effects 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
238000005660 chlorination reaction Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
UGHIQYNKFXEQPU-UHFFFAOYSA-N 2,3-dichloro-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Cl)=C1Cl UGHIQYNKFXEQPU-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
VMMUHZZNIYRBPI-UHFFFAOYSA-N 1,3,4-trichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C(Cl)=C1Cl VMMUHZZNIYRBPI-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
239000012264 purified product Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
CTSQZGJZQUVGBQ-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3,6-dimethylbenzene Chemical group CC1=C(Cl)C(Cl)=C(C)C(Cl)=C1Cl CTSQZGJZQUVGBQ-UHFFFAOYSA-N 0.000 description 1
DMXBTUVHCAMVQL-UHFFFAOYSA-N 1,3-dichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C(Cl)=C1 DMXBTUVHCAMVQL-UHFFFAOYSA-N 0.000 description 1
FIMVMYXUGWSJKE-UHFFFAOYSA-N 1,4-xylene Chemical group CC1=CC=C(C)C=C1.CC1=CC=C(C)C=C1 FIMVMYXUGWSJKE-UHFFFAOYSA-N 0.000 description 1
KZNRNQGTVRTDPN-UHFFFAOYSA-N 2-chloro-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Cl)=C1 KZNRNQGTVRTDPN-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
238000007664 blowing Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
UHUWQCGPGPPDDT-UHFFFAOYSA-N greigite Chemical compound [S-2].[S-2].[S-2].[S-2].[Fe+2].[Fe+3].[Fe+3] UHUWQCGPGPPDDT-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
KAEAMHPPLLJBKF-UHFFFAOYSA-N iron(3+) sulfide Chemical compound [S-2].[S-2].[S-2].[Fe+3].[Fe+3] KAEAMHPPLLJBKF-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052960 marcasite Inorganic materials 0.000 description 1
-1 p-xylene p-xylene p-xylene chlorine Chemical compound 0.000 description 1
150000002938 p-xylenes Chemical class 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
NIFIFKQPDTWWGU-UHFFFAOYSA-N pyrite Chemical compound [Fe+2].[S-][S-] NIFIFKQPDTWWGU-UHFFFAOYSA-N 0.000 description 1
229910052683 pyrite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
- C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/427—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
- C07C49/443—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH133376A 1975-02-04 1976-02-03 Process for the preparation of 2,5-dichloro-p-xylene. CH619913A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US54706675A	1975-02-04	1975-02-04

Publications (1)

Publication Number	Publication Date
CH619913A5 true CH619913A5 (en)	1980-10-31

Family

ID=24183212

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH133376A CH619913A5 (en)	1975-02-04	1976-02-03	Process for the preparation of 2,5-dichloro-p-xylene.

Country Status (11)

Country	Link
JP (1)	JPS5953246B2 (it)
BE (1)	BE838198A (it)
BR (1)	BR7600572A (it)
CA (1)	CA1081713A (it)
CH (1)	CH619913A5 (it)
DE (1)	DE2604278C2 (it)
FR (1)	FR2300058A1 (it)
GB (1)	GB1492162A (it)
IT (1)	IT1057596B (it)
NL (1)	NL7600938A (it)
SU (2)	SU637075A3 (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH05332871A (ja) *	1992-06-01	1993-12-17	Tokinori Tsuda	指圧計

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3692850A (en) *	1970-07-31	1972-09-19	Tenneco Chem	Process for the production of 2,4,5-trichlorotoluene
IT1022654B (it) *	1973-10-17	1978-04-20	Hooker Chemicals Plastics Corp	Catalizzatori di orientamento di isomere per la alogenazione di idrocarburi aromatici

1976
- 1976-01-29 BR BR7600572A patent/BR7600572A/pt unknown
- 1976-01-30 NL NL7600938A patent/NL7600938A/xx not_active Application Discontinuation
- 1976-01-30 CA CA244,979A patent/CA1081713A/en not_active Expired
- 1976-02-02 IT IT1980276A patent/IT1057596B/it active
- 1976-02-02 BE BE164034A patent/BE838198A/xx not_active IP Right Cessation
- 1976-02-02 FR FR7602762A patent/FR2300058A1/fr not_active Withdrawn
- 1976-02-03 GB GB427576A patent/GB1492162A/en not_active Expired
- 1976-02-03 CH CH133376A patent/CH619913A5/de not_active IP Right Cessation
- 1976-02-03 SU SU762318204A patent/SU637075A3/ru active
- 1976-02-03 JP JP1121276A patent/JPS5953246B2/ja not_active Expired
- 1976-02-04 SU SU762319160A patent/SU791219A3/ru active
- 1976-02-04 DE DE19762604278 patent/DE2604278C2/de not_active Expired

Also Published As

Publication number	Publication date
DE2604278A1 (de)	1976-08-05
SU637075A3 (ru)	1978-12-05
NL7600938A (nl)	1976-08-06
GB1492162A (en)	1977-11-16
JPS5953246B2 (ja)	1984-12-24
BE838198A (fr)	1976-08-02
DE2604278C2 (de)	1984-07-05
IT1057596B (it)	1982-03-30
JPS51101926A (ja)	1976-09-08
BR7600572A (pt)	1976-08-31
CA1081713A (en)	1980-07-15
FR2300058A1 (fr)	1976-09-03
SU791219A3 (ru)	1980-12-23

Legal Events

Date	Code	Title	Description
1982-12-15	PFA	Name/firm changed	Owner name: OCCIDENTAL CHEMICAL CORPORATION
1986-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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CH622759A5 (it)	1981-04-30
DE1493815A1 (de)	1969-06-04	Verfahren zur Herstellung von Bisphenol aus harzartigen Nebenprodukten
DE2635174C2 (de)	1985-10-24	Verfahren zur Herstellung von Butandiol und/oder Butendiol
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DD150741A5 (de)	1981-09-16	Verfahren zur herstellung von 2',6'-dialkyl-n-(alkoxymethyl)-2-chloracetaniliden
DE2644641C2 (de)	1983-09-29	Verfahren zur Herstellung von bestimmten kernchlorierten Benzotrichloriden
CH619913A5 (en)	1980-10-31	Process for the preparation of 2,5-dichloro-p-xylene.
DE2527289A1 (de)	1976-01-29	Verfahren zur herstellung von alkylacetophenonen
EP0057844A1 (de)	1982-08-18	Verfahren zur Herstellung von Polychlorbenzoylchloriden
DE2057956A1 (de)	1972-06-08	Verfahren zur Herstellung von aliphatischen Carbonsaeurechloriden
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DE2756235C2 (de)	1986-12-04	Verfahren zur Herstellung von gegebenenfalls substituiertem Benzotrifluorid
DE2612115A1 (de)	1976-10-14	Verfahren zur herstellung von m- aryloxy-benzyl-bromiden
DE2847104A1 (de)	1979-06-28	Verfahren zur herstellung von 2,2-bis (4-hydroxyphenyl)-propan aus den destillationsnebenprodukten desselben
DE1418334B1 (de)	1971-01-07	Verfahren zur Herstellung von 1,2,3,4,7,7-Hexachlorbicyclo[2,2,1]-2,5-heptadien aus Hexachlorcyclopentadien und Acetylen
DE2708388A1 (de)	1978-08-31	Verfahren zur herstellung von 4,4'- dihydroxydiphenylsulfon
DE3016119C2 (it)	1988-07-21
DE1026524B (de)	1958-03-20	Verfahren zur Herstellung von Polymerisaten aus Olefinen
DE954873C (de)	1956-12-27	Verfahren zur Herstellung von Diaethylisonitrosomalonat
DE1189975B (de)	1965-04-01	Verfahren zur Herstellung von beta, beta'-Dicyandiaethylaether
EP0014406B1 (de)	1981-08-26	Verfahren zur Abtrennung von Selen, Selenverbindungen, Schwefel und/oder Schwefelverbindungen aus diese Elemente bzw. Verbindungen aufweisenden Urethanen
DE2743004A1 (de)	1978-04-06	Verfahren zur herstellung aromatischer carbonsaeuren oder deren methylester