CA1155873A - Methode et installation de production de vinyltoluene - Google Patents

Methode et installation de production de vinyltoluene

Info

Publication number: CA1155873A
Authority: CA; Canada
Prior art keywords: vinyltoluene; crude; inhibitor; vaporous; condensed
Prior art date: 1980-12-30
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

CA000393024A

Other languages

English (en)

Inventor

James M. Watson

Darrell E. Bailey

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.)

Cosden Technology Inc

Original Assignee

Cosden Technology Inc

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.)

1980-12-30

Filing date

1981-12-22

Publication date

1983-10-25

1981-12-22 Application filed by Cosden Technology Inc filed Critical Cosden Technology Inc

1983-10-25 Application granted granted Critical

1983-10-25 Publication of CA1155873A publication Critical patent/CA1155873A/fr

Status Expired legal-status Critical Current

Links

HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 title claims abstract description 127
238000000034 method Methods 0.000 title claims abstract description 30
238000004519 manufacturing process Methods 0.000 title claims abstract description 18
230000008569 process Effects 0.000 title claims description 25
239000003112 inhibitor Substances 0.000 claims abstract description 64
238000006116 polymerization reaction Methods 0.000 claims abstract description 26
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 24
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 claims abstract description 22
239000008346 aqueous phase Substances 0.000 claims abstract description 15
239000012074 organic phase Substances 0.000 claims abstract description 13
238000001914 filtration Methods 0.000 claims abstract description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
238000004821 distillation Methods 0.000 claims description 38
HIQCTHFRLRVNPP-UHFFFAOYSA-N 4-methyl-2,3-dinitrophenol Chemical compound CC1=CC=C(O)C([N+]([O-])=O)=C1[N+]([O-])=O HIQCTHFRLRVNPP-UHFFFAOYSA-N 0.000 claims description 3
238000004064 recycling Methods 0.000 claims description 3
238000000746 purification Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 27
229920000642 polymer Polymers 0.000 abstract description 26
239000000047 product Substances 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 13
HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000010791 quenching Methods 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 4
238000013461 design Methods 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
230000035508 accumulation Effects 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
238000005194 fractionation Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
230000003405 preventing effect Effects 0.000 description 3
239000000523 sample Substances 0.000 description 3
239000011269 tar Substances 0.000 description 3
238000012546 transfer Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
241000482268 Zea mays subsp. mays Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000010586 diagram Methods 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
-1 vinyl- Chemical group 0.000 description 2
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
MAQGNTACXAOLNE-UHFFFAOYSA-N 2-hydroxy-5-methyl-3-nitrobenzoic acid Chemical compound CC1=CC(C(O)=O)=C(O)C([N+]([O-])=O)=C1 MAQGNTACXAOLNE-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
KSHJAFFDLKPUMT-UHFFFAOYSA-N dinitro-ortho-cresol Chemical compound CC1=C(O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KSHJAFFDLKPUMT-UHFFFAOYSA-N 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920002102 polyvinyl toluene Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000012719 thermal polymerization Methods 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000013022 venting Methods 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Analytical Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Water Supply & Treatment (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000393024A 1980-12-30 1981-12-22 Methode et installation de production de vinyltoluene Expired CA1155873A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US221,662		1980-12-30
US22166280A	1980-12-31	1980-12-31

Publications (1)

Publication Number	Publication Date
CA1155873A true CA1155873A (fr)	1983-10-25

Family

ID=22828774

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000393024A Expired CA1155873A (fr)	1980-12-30	1981-12-22	Methode et installation de production de vinyltoluene

Country Status (7)

Country	Link
JP (1)	JPS57134424A (fr)
BE (1)	BE891574A (fr)
CA (1)	CA1155873A (fr)
DE (1)	DE3151976A1 (fr)
FR (1)	FR2497193B1 (fr)
GB (1)	GB2090282B (fr)
IT (1)	IT1142638B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4558169A (en) *	1980-12-31	1985-12-10	Cosden Technology, Inc.	Process for the production of vinyltoluene

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1074757A (fr) *	1952-02-28	1954-10-08	Dow Chemical Co	Perfectionnements apportés à la préparation du méthylstyrolène
US4105506A (en) *	1977-02-24	1978-08-08	Cosden Technology, Inc.	Polymerization inhibitor for vinyl aromatic compounds

1981
- 1981-12-22 BE BE2/206898A patent/BE891574A/fr not_active IP Right Cessation
- 1981-12-22 CA CA000393024A patent/CA1155873A/fr not_active Expired
- 1981-12-22 GB GB8138592A patent/GB2090282B/en not_active Expired
- 1981-12-24 IT IT25852/81A patent/IT1142638B/it active
- 1981-12-24 JP JP56208264A patent/JPS57134424A/ja active Pending
- 1981-12-30 DE DE19813151976 patent/DE3151976A1/de not_active Withdrawn
- 1981-12-30 FR FR8124477A patent/FR2497193B1/fr not_active Expired

Also Published As

Publication number	Publication date
DE3151976A1 (de)	1982-08-12
GB2090282A (en)	1982-07-07
GB2090282B (en)	1983-11-02
FR2497193A1 (fr)	1982-07-02
IT1142638B (it)	1986-10-08
BE891574A (fr)	1982-04-16
JPS57134424A (en)	1982-08-19
FR2497193B1 (fr)	1985-06-28
IT8125852A0 (it)	1981-12-24

Legal Events

Date	Code	Title	Description
2000-10-25	MKEX	Expiry

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EP0062626B1 (fr)	1985-06-19	Procédé de distillation de vinyltoluène
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US4492675A (en)	1985-01-08	Apparatus for the production of vinyltoluene
US3462347A (en)	1969-08-19	Solvent purification and recovery by stripping and distillation
US4442048A (en)	1984-04-10	Method and apparatus for controlling the formation of polymer accumulations during distillation of a vinylaromatic monomer
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US6348136B1 (en)	2002-02-19	Method and apparatus for the purification of vinyl aromatic compounds
US4418191A (en)	1983-11-29	Solvent purification
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US8524046B2 (en)	2013-09-03	Distillation column pressure control
US4514261A (en)	1985-04-30	Refining of tertiary butylstyrene
US2473203A (en)	1949-06-14	Diolefin distillation
EP1966112B1 (fr)	2009-05-27	Procede ameliore de deshydrogenation d'hydrocarbures alkyl-aromatiques pour la fabrication de monomeres vinyl-aromatiques
US3408266A (en)	1968-10-29	Sub-atmospheric distillation of a benzene, toluene, ethylbenzene styrene mixture in a single column
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FI56961C (fi)	1980-05-12	Foerfarande foer tillsaettande av svavel vid en process foer fraktionerad destillation av en blandning innehaollande polymeriserbara foereningar