NL8000580A - Werkwijze voor de bereiding van sec-butanol uit lineaire butenen. - Google Patents
Werkwijze voor de bereiding van sec-butanol uit lineaire butenen. Download PDFInfo
- Publication number
- NL8000580A NL8000580A NL8000580A NL8000580A NL8000580A NL 8000580 A NL8000580 A NL 8000580A NL 8000580 A NL8000580 A NL 8000580A NL 8000580 A NL8000580 A NL 8000580A NL 8000580 A NL8000580 A NL 8000580A
- Authority
- NL
- Netherlands
- Prior art keywords
- sec
- butanol
- water
- linear
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 title abstract description 36
- 238000002360 preparation method Methods 0.000 title description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003729 cation exchange resin Substances 0.000 abstract description 4
- 239000007791 liquid phase Substances 0.000 abstract description 4
- 150000007524 organic acids Chemical class 0.000 abstract description 4
- 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 abstract description 3
- 238000010533 azeotropic distillation Methods 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- VPSLGSSVPWVZFG-UHFFFAOYSA-N butan-2-yl propanoate Chemical compound CCC(C)OC(=O)CC VPSLGSSVPWVZFG-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001174 sulfone group Chemical group 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000010931 ester hydrolysis Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- -1 olefins esters Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000012808 vapor phase 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
-
- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1970679 | 1979-01-30 | ||
| IT19706/79A IT1110745B (it) | 1979-01-30 | 1979-01-30 | Procedimento per la sintesi di sec-butanolo da buteni lineari |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8000580A true NL8000580A (nl) | 1980-08-01 |
Family
ID=11160539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8000580A NL8000580A (nl) | 1979-01-30 | 1980-01-30 | Werkwijze voor de bereiding van sec-butanol uit lineaire butenen. |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS55102530A (sv) |
| BE (1) | BE881437A (sv) |
| DE (1) | DE3003126A1 (sv) |
| DK (1) | DK35080A (sv) |
| ES (1) | ES488741A0 (sv) |
| FR (1) | FR2447896A1 (sv) |
| GB (1) | GB2041364B (sv) |
| IT (1) | IT1110745B (sv) |
| NL (1) | NL8000580A (sv) |
| NO (1) | NO800215L (sv) |
| SE (1) | SE8000742L (sv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054576B2 (en) * | 1980-12-18 | 1988-07-13 | Union Explosivos Rio Tinto, S.A. | Process for producing esters from olefins |
| US4384148A (en) * | 1982-02-26 | 1983-05-17 | Uop Inc. | Hydration of olefins |
| US4927954A (en) * | 1983-06-28 | 1990-05-22 | Union Carbide Chemicals And Plastics Company, Inc. | Continuous process for producing secondary alcohols and carboxylic acid esters |
| DE69117871T2 (de) * | 1990-10-31 | 1996-11-07 | Daicel Chem | Verfahren zur Herstellung eines Niedrigalkylacetats |
| RU2206560C1 (ru) * | 2001-12-27 | 2003-06-20 | Закрытое акционерное общество фирма "Альен" | Способ получения вторичного бутилового спирта |
| EP2046706A1 (de) * | 2006-07-20 | 2009-04-15 | Basf Se | Verfahren zur herstellung von isopropanol und 2-butanol aus den entsprechenden alkanen |
| JPWO2010071011A1 (ja) * | 2008-12-15 | 2012-05-24 | Ｊｘ日鉱日石エネルギー株式会社 | 酢酸エステルの製造方法 |
| CN104311390A (zh) * | 2014-10-17 | 2015-01-28 | 深圳市飞扬实业有限公司 | 一种合成仲丁醇的方法 |
| RU2570818C1 (ru) | 2015-01-12 | 2015-12-10 | Открытое акционерное общество "Газпромнефть - Московский НПЗ" | Способ получения карбонильных соединений с2-с4 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1374368A (en) * | 1972-08-15 | 1974-11-20 | Bp Chem Int Ltd | Production of secbutanol |
-
1979
- 1979-01-30 IT IT19706/79A patent/IT1110745B/it active
-
1980
- 1980-01-16 GB GB8001408A patent/GB2041364B/en not_active Expired
- 1980-01-28 FR FR8001798A patent/FR2447896A1/fr not_active Withdrawn
- 1980-01-28 DK DK35080A patent/DK35080A/da not_active Application Discontinuation
- 1980-01-29 ES ES488741A patent/ES488741A0/es active Granted
- 1980-01-29 DE DE19803003126 patent/DE3003126A1/de not_active Ceased
- 1980-01-29 JP JP837480A patent/JPS55102530A/ja active Pending
- 1980-01-29 NO NO800215A patent/NO800215L/no unknown
- 1980-01-30 SE SE8000742A patent/SE8000742L/sv not_active Application Discontinuation
- 1980-01-30 BE BE0/199176A patent/BE881437A/fr not_active IP Right Cessation
- 1980-01-30 NL NL8000580A patent/NL8000580A/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55102530A (en) | 1980-08-05 |
| BE881437A (fr) | 1980-07-30 |
| GB2041364B (en) | 1983-03-23 |
| IT7919706A0 (it) | 1979-01-30 |
| IT1110745B (it) | 1986-01-06 |
| DE3003126A1 (de) | 1980-07-31 |
| FR2447896A1 (fr) | 1980-08-29 |
| DK35080A (da) | 1980-07-31 |
| GB2041364A (en) | 1980-09-10 |
| NO800215L (no) | 1980-07-31 |
| SE8000742L (sv) | 1980-07-31 |
| ES8103006A1 (es) | 1981-02-16 |
| ES488741A0 (es) | 1981-02-16 |
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