PL57568B1 - - Google Patents

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Publication number: PL57568B1
Authority: PL; Poland
Prior art keywords: propylene; alcohol; reaction; acrolein; zone
Prior art date: 1966-07-15

Application number

PL115620A

Other languages

English (en)

Polish (pl)

Inventor

Janusz Beres mgr

inz. Gerard Bekierz mgr

inz. Jacek netper mgr

Cieszynski Henryk

Original Assignee

Instytut Ciezkiej Syntezy Organicznej

Filing date

1966-07-15

Publication date

1969-04-28

1966-07-15 Application filed by Instytut Ciezkiej Syntezy Organicznej filed Critical Instytut Ciezkiej Syntezy Organicznej

1967-07-13 Priority to CS5159A priority Critical patent/CS167869B2/cs

1967-07-13 Priority to FR114312A priority patent/FR1531137A/fr

1967-07-14 Priority to DE1668251A priority patent/DE1668251C3/de

1969-04-28 Publication of PL57568B1 publication Critical patent/PL57568B1/pl

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 36
HGINCPLSRVDWNT-UHFFFAOYSA-N acrylaldehyde Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 27
239000003054 catalyst Substances 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 22
XXROGKLTLUQVRX-UHFFFAOYSA-N Allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 21
BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 17
238000007254 oxidation reaction Methods 0.000 claims description 16
NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 15
230000003647 oxidation Effects 0.000 claims description 13
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000003638 reducing agent Substances 0.000 claims description 9
229910052739 hydrogen Chemical class 0.000 claims description 7
239000001257 hydrogen Chemical class 0.000 claims description 6
239000011261 inert gas Substances 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 4
238000004821 distillation Methods 0.000 claims description 4
125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 3
238000006555 catalytic reaction Methods 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
-1 n-propylene alcohol Chemical compound 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000000075 primary alcohol group Chemical class 0.000 claims 1
150000003333 secondary alcohols Chemical class 0.000 claims 1
235000019441 ethanol Nutrition 0.000 description 28
239000007789 gas Substances 0.000 description 23
238000000034 method Methods 0.000 description 22
IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 14
239000000047 product Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
239000012263 liquid product Substances 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
239000001294 propane Substances 0.000 description 4
239000002994 raw material Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
230000003197 catalytic Effects 0.000 description 2
238000011068 load Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
239000011733 molybdenum Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000002194 synthesizing Effects 0.000 description 2
229910052718 tin Inorganic materials 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
210000000988 Bone and Bones Anatomy 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
GELKBWJHTRAYNV-UHFFFAOYSA-K Lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L Magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N N-Propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
241000658540 Ora Species 0.000 description 1
DJWUNCQRNNEAKC-UHFFFAOYSA-L Zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
238000001354 calcination Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
239000010949 copper Substances 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000000895 extractive distillation Methods 0.000 description 1
230000002349 favourable Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910001386 lithium phosphate Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
239000011776 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
230000000737 periodic Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000002035 prolonged Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1

PL115620A 1966-07-15 1966-07-15 PL57568B1 (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CS5159A CS167869B2 (de)	1966-07-15	1967-07-13
FR114312A FR1531137A (fr)	1966-07-15	1967-07-13	Procédé de production d'alcools
DE1668251A DE1668251C3 (de)	1966-07-15	1967-07-14	Verfahren zur Herstellung Allylalkohol aus Propylen

Publications (1)

Publication Number	Publication Date
PL57568B1 true PL57568B1 (de)	1969-04-28

Publication	Publication Date	Title
US7348459B2 (en)	2008-03-25	Process for the preparation of 3,3-dimethylbutanal
JP2574406B2 (ja)	1997-01-22	メタクリル酸の製法
CN103328428A (zh)	2013-09-25	制备丙烯醛/丙烯酸的改进方法
JP4368454B2 (ja)	2009-11-18	アルコールの製造法
CA1162566A (en)	1984-02-21	Processes for producing 7-octen-1-al and derivatives thereof
GB2025418A (en)	1980-01-23	Methanol from synthesis gas
JP2022541622A (ja)	2022-09-26	プロペンから標的生成物としてアクロレイン又はアクリル酸のいずれかを連続的に生成するための方法
JPS58246A (ja)	1983-01-05	アルコ−ルのカルボニル化用触媒
SU583739A3 (ru)	1977-12-05	Способ получени ненасыщенных эфиров карбоновых кислот
EP0151886A1 (de)	1985-08-21	Verfahren zur Herstellung von Estern
PL57568B1 (de)	1969-04-28
CN1059194C (zh)	2000-12-06	一种气相加氢制1,4-丁二醇的方法
JPS6032615B2 (ja)	1985-07-29	プロピレンの接触気相酸化によるアクリル酸の製造方法
US4226790A (en)	1980-10-07	Process for oxidizing thallium (I) to thallium (III)
US3981931A (en)	1976-09-21	Diols by transesterification using magnesia catalysts
GB2059419A (en)	1981-04-23	Production of organic saturated aliphatic monocarboxylic acids
EP0012800B1 (de)	1981-09-16	Verfahren zur Herstellung von Butan-2,3-dion und Aceton aus Isobutanal
US4980501A (en)	1990-12-25	Production of secondary-butyl fluoroester and secondary-butyl alcohol obtained therefrom
CA1050049A (en)	1979-03-06	Process for preparing allylic alcohols
SU782297A1 (ru)	1984-02-07	Способ получени метилэтилкетона
EP1586548B1 (de)	2009-06-10	Verfahren zur Herstellung von 3,3-Dimethylbutanal
SU644373A3 (ru)	1979-01-25	Способ получени диметилтерефталата
SU120513A1 (ru)	1958-11-30	Способ получени пара-нитроацетофенона
SU675759A1 (ru)	1985-06-23	Способ получени циклогексанона и циклогексанола
CN114230458A (zh)	2022-03-25	一种环己烷空气催化氧化生成的醇酮酸复杂氧化产物分离的方法

PL57568B1 - - Google Patents

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Priority Applications (3)

Publications (1)

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