CA1298844C - Procede pour la production de 1,4-dioxane - Google Patents

Procede pour la production de 1,4-dioxane

Info

Publication number: CA1298844C
Authority: CA; Canada
Prior art keywords: reaction; pressure; dioxane; reactor; glycol
Prior art date: 1988-08-12
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 - Fee Related

Application number

CA000574566A

Other languages

English (en)

Inventor

Albert J. Heuvelsland

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.)

Dow Chemical Nederland BV

Dow Chemical Co

Original Assignee

Dow Chemical Nederland BV

Dow Chemical Co

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.)

1988-08-12

Filing date

1988-08-12

Publication date

1992-04-14

1988-08-12 Application filed by Dow Chemical Nederland BV, Dow Chemical Co filed Critical Dow Chemical Nederland BV

1988-08-12 Priority to CA000574566A priority Critical patent/CA1298844C/fr

1992-04-14 Application granted granted Critical

1992-04-14 Publication of CA1298844C publication Critical patent/CA1298844C/fr

2009-04-14 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 42
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 title claims abstract description 29
239000003054 catalyst Substances 0.000 claims abstract description 27
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 24
238000006297 dehydration reaction Methods 0.000 claims abstract description 23
230000018044 dehydration Effects 0.000 claims abstract description 18
239000000203 mixture Substances 0.000 claims abstract description 14
239000007788 liquid Substances 0.000 claims abstract description 7
239000012429 reaction media Substances 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 44
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 36
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
239000000376 reactant Substances 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 7
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
-1 glycol compound Chemical class 0.000 claims 3
125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
239000011269 tar Substances 0.000 abstract description 14
230000015572 biosynthetic process Effects 0.000 abstract description 12
238000005187 foaming Methods 0.000 abstract description 10
229920001223 polyethylene glycol Polymers 0.000 abstract description 6
239000002202 Polyethylene glycol Substances 0.000 abstract description 5
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 abstract description 2
239000002253 acid Substances 0.000 abstract description 2
238000010924 continuous production Methods 0.000 abstract description 2
239000000047 product Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
239000006227 byproduct Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
230000007812 deficiency Effects 0.000 description 4
HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
229910004014 SiF4 Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000005485 electric heating Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1

Landscapes

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

CA000574566A 1988-08-12 1988-08-12 Procede pour la production de 1,4-dioxane Expired - Fee Related CA1298844C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000574566A CA1298844C (fr)	1988-08-12	1988-08-12	Procede pour la production de 1,4-dioxane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000574566A CA1298844C (fr)	1988-08-12	1988-08-12	Procede pour la production de 1,4-dioxane

Publications (1)

Publication Number	Publication Date
CA1298844C true CA1298844C (fr)	1992-04-14

Family

ID=4138538

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000574566A Expired - Fee Related CA1298844C (fr)	1988-08-12	1988-08-12	Procede pour la production de 1,4-dioxane

Country Status (1)

Country	Link
CA (1)	CA1298844C (fr)

1988
- 1988-08-12 CA CA000574566A patent/CA1298844C/fr not_active Expired - Fee Related

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Legal Events

Date	Code	Title	Description
1994-10-14	MKLA	Lapsed