TW200418769A - Process for preparing tert-butanol - Google Patents

Process for preparing tert-butanol Download PDF

Info

Publication number: TW200418769A
Authority: TW; Taiwan
Prior art keywords: water; reactor; isobutene; butanol; reaction
Prior art date: 2002-12-19

Application number

TW092135452A

Other languages

English (en)

Chinese (zh)

Inventor

Silvia Santiago Fernandez

Bernhard Scholz

Franz Nierlich

Alfred Kaizik

Wilfried Buschken

Dieter Reusch

Andreas Beckmann

Original Assignee

Oxeno Olefinchemie Gmbh

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.)

2002-12-19

Filing date

2003-12-15

Publication date

2004-10-01

2003-12-15 Application filed by Oxeno Olefinchemie Gmbh filed Critical Oxeno Olefinchemie Gmbh

2004-10-01 Publication of TW200418769A publication Critical patent/TW200418769A/zh

Links

DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 title claims abstract description 53
238000004519 manufacturing process Methods 0.000 title abstract description 23
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 172
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 144
239000000203 mixture Substances 0.000 claims abstract description 77
238000006243 chemical reaction Methods 0.000 claims abstract description 72
229930195733 hydrocarbon Natural products 0.000 claims abstract description 37
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 37
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 30
230000002378 acidificating effect Effects 0.000 claims abstract description 12
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 claims abstract description 10
239000003456 ion exchange resin Substances 0.000 claims abstract description 10
229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims description 37
239000011541 reaction mixture Substances 0.000 claims description 20
230000007423 decrease Effects 0.000 claims description 8
238000004064 recycling Methods 0.000 claims description 8
239000008240 homogeneous mixture Substances 0.000 abstract description 8
239000003054 catalyst Substances 0.000 description 36
239000000047 product Substances 0.000 description 25
239000011347 resin Substances 0.000 description 14
229920005989 resin Polymers 0.000 description 14
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 12
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 11
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 10
239000012071 phase Substances 0.000 description 10
239000007788 liquid Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
150000001336 alkenes Chemical class 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
230000000052 comparative effect Effects 0.000 description 7
239000002245 particle Substances 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012456 homogeneous solution Substances 0.000 description 5
239000001282 iso-butane Substances 0.000 description 5
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 4
230000008901 benefit Effects 0.000 description 4
238000006703 hydration reaction Methods 0.000 description 4
238000010587 phase diagram Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000001273 butane Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000010586 diagram Methods 0.000 description 3
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
230000036571 hydration Effects 0.000 description 3
238000006384 oligomerization reaction Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000012545 processing Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000010517 secondary reaction Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
101100424627 Caenorhabditis elegans mec-12 gene Proteins 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000009826 distribution Methods 0.000 description 2
230000007774 longterm Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
125000000542 sulfonic acid group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
HQCNSHPBVRWXGH-UHFFFAOYSA-N 2-methylprop-1-ene;hydrate Chemical compound O.CC(C)=C HQCNSHPBVRWXGH-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical compound C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000000475 acetylene derivatives Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
-1 alkali metal salt Chemical class 0.000 description 1
238000005865 alkene metathesis reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000005034 decoration Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000007210 heterogeneous catalysis Methods 0.000 description 1
239000011964 heteropoly acid Substances 0.000 description 1
238000007172 homogeneous catalysis Methods 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000003999 initiator Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
QSGNIZYSOOADSE-UHFFFAOYSA-N penta-1,4-dienylbenzene Chemical compound C=CCC=CC1=CC=CC=C1 QSGNIZYSOOADSE-UHFFFAOYSA-N 0.000 description 1
150000002976 peresters Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
229910052704 radon Inorganic materials 0.000 description 1
SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
238000012958 reprocessing Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds

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)

TW092135452A 2002-12-19 2003-12-15 Process for preparing tert-butanol TW200418769A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10259413		2002-12-19
DE10330710A DE10330710A1 (de)	2002-12-19	2003-07-08	Verfahren zur Herstellung von tert.-Butanol

Publications (1)

Publication Number	Publication Date
TW200418769A true TW200418769A (en)	2004-10-01

Family

ID=32403935

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW092135452A TW200418769A (en)	2002-12-19	2003-12-15	Process for preparing tert-butanol

Country Status (3)

Country	Link
AT (1)	ATE455744T1 (de)
DE (2)	DE10330710A1 (de)
TW (1)	TW200418769A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10338581A1 (de)	2003-08-22	2005-03-17	Oxeno Olefinchemie Gmbh	Verfahren zur Erzeugung von tert.-Butanol
DE102004030943B4 (de) *	2004-06-26	2013-10-02	Evonik Oxeno Gmbh	Verfahren zur Herstellung von tert.-Butanol aus Isobuten-haltigen Kohlenwasserstoffgemischen
DE102011005608A1 (de)	2011-03-16	2012-09-20	Evonik Oxeno Gmbh	Mischoxidzusammensetzungen und Verfahren zur Herstellung von Isoolefinen

2003
- 2003-07-08 DE DE10330710A patent/DE10330710A1/de not_active Withdrawn
- 2003-10-22 AT AT03103901T patent/ATE455744T1/de not_active IP Right Cessation
- 2003-10-22 DE DE50312354T patent/DE50312354D1/de not_active Expired - Lifetime
- 2003-12-15 TW TW092135452A patent/TW200418769A/zh unknown

Also Published As

Publication number	Publication date
DE10330710A1 (de)	2004-07-01
ATE455744T1 (de)	2010-02-15
DE50312354D1 (de)	2010-03-11

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