CA1077965A - Procede pour la production de chloroprene - Google Patents

Procede pour la production de chloroprene

Info

Publication number: CA1077965A
Authority: CA; Canada
Prior art keywords: dichlorobutene; butadiene; separation; higher boiling; reaction mixture
Prior art date: 1977-11-10
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

CA290,585A

Other languages

English (en)

Inventor

Hideki Matsumura

Takao Iwasaki

Junji Hirano

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.)

Denka Co Ltd

Original Assignee

Denki Kagaku Kogyo KK

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.)

1977-11-10

Filing date

1977-11-10

Publication date

1980-05-20

1977-11-10 Application filed by Denki Kagaku Kogyo KK filed Critical Denki Kagaku Kogyo KK

1977-11-10 Priority to CA290,585A priority Critical patent/CA1077965A/fr

1980-05-20 Application granted granted Critical

1980-05-20 Publication of CA1077965A publication Critical patent/CA1077965A/fr

Status Expired legal-status Critical Current

Links

YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 title claims abstract description 24
238000000034 method Methods 0.000 title claims description 24
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 106
238000009835 boiling Methods 0.000 claims abstract description 48
150000001875 compounds Chemical class 0.000 claims abstract description 40
XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 claims abstract description 37
238000000926 separation method Methods 0.000 claims abstract description 34
239000011541 reaction mixture Substances 0.000 claims abstract description 25
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims abstract description 13
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims abstract description 12
FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 claims description 15
230000006872 improvement Effects 0.000 claims description 4
238000006317 isomerization reaction Methods 0.000 abstract description 13
238000005660 chlorination reaction Methods 0.000 abstract description 10
239000002585 base Substances 0.000 description 10
239000011269 tar Substances 0.000 description 9
GBQWGHDWLUYAEG-UHFFFAOYSA-N 1,1,1,2,2-pentachlorobutane Chemical compound CCC(Cl)(Cl)C(Cl)(Cl)Cl GBQWGHDWLUYAEG-UHFFFAOYSA-N 0.000 description 8
239000005539 carbonized material Substances 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
WSPZFVOCHITLIY-UHFFFAOYSA-N 2,2,3,3-tetrachlorobutane Chemical compound CC(Cl)(Cl)C(C)(Cl)Cl WSPZFVOCHITLIY-UHFFFAOYSA-N 0.000 description 6
AKQZPPKQVZVYCC-UHFFFAOYSA-N 4,4,4-trichlorobut-1-ene Chemical compound ClC(Cl)(Cl)CC=C AKQZPPKQVZVYCC-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000007790 solid phase Substances 0.000 description 6
UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical compound CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 4
HSEFPJMMKNHABB-UHFFFAOYSA-N 2-chlorobut-1-ene Chemical compound CCC(Cl)=C HSEFPJMMKNHABB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000539 dimer Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
230000006641 stabilisation Effects 0.000 description 3
238000011105 stabilization Methods 0.000 description 3
-1 tetrachlorbutane Chemical compound 0.000 description 3
SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 2
PCPYTNCQOSFKGG-UHFFFAOYSA-N 1-chlorobuta-1,3-diene Chemical compound ClC=CC=C PCPYTNCQOSFKGG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
SWSOIFQIPTXLOI-HNQUOIGGSA-N (e)-1,4-dichlorobut-1-ene Chemical compound ClCC\C=C\Cl SWSOIFQIPTXLOI-HNQUOIGGSA-N 0.000 description 1
IXZVKECRTHXEEW-UHFFFAOYSA-N 1,2,3,4-tetrachlorobutane Chemical compound ClCC(Cl)C(Cl)CCl IXZVKECRTHXEEW-UHFFFAOYSA-N 0.000 description 1
RMISVOPUIFJTEO-UHFFFAOYSA-N 2,3-dichlorobutane Chemical compound CC(Cl)C(C)Cl RMISVOPUIFJTEO-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
238000007033 dehydrochlorination reaction Methods 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

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

CA290,585A 1977-11-10 1977-11-10 Procede pour la production de chloroprene Expired CA1077965A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA290,585A CA1077965A (fr)	1977-11-10	1977-11-10	Procede pour la production de chloroprene

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA290,585A CA1077965A (fr)	1977-11-10	1977-11-10	Procede pour la production de chloroprene

Publications (1)

Publication Number	Publication Date
CA1077965A true CA1077965A (fr)	1980-05-20

Family

ID=4109993

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA290,585A Expired CA1077965A (fr)	1977-11-10	1977-11-10	Procede pour la production de chloroprene

Country Status (1)

Country	Link
CA (1)	CA1077965A (fr)

1977
- 1977-11-10 CA CA290,585A patent/CA1077965A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-05-20	MKEX	Expiry

Publication	Publication Date	Title
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EP0004636B1 (fr)	1982-07-07	Procédé de préparation de benzotrifluoride et ses dérivés
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US2649472A (en)	1953-08-18	Process for producing acrylonitrile
CA1077965A (fr)	1980-05-20	Procede pour la production de chloroprene
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JPH0585968A (ja)	1993-04-06	ヒドロゲンペルフルオロアルカンの合成
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US2662924A (en)	1953-12-15	Dehydrochlorination of polychlorocyclohexanes
US2369485A (en)	1945-02-13	Process for producing unsaturated chlorinated hydrocarbons
US2387341A (en)	1945-10-23	Bromination of 2,6-nitro chlor toluene
US3061653A (en)	1962-10-30	Preparation of 2, 3-dichlorobutadiene-1, 3
JPH0230298B2 (fr)	1990-07-05
US2725404A (en)	1955-11-29	Dehydrochlorination of benzene hexachloride