DE1468802C3 - Verfahren zur Oxychlorierung von aliphatischen Kohlenwasserstoffen, die 1 bis 4 Kohlenstoff atome aufweisen, oder ihrer teilweise chlorierten Derivate - Google Patents

Verfahren zur Oxychlorierung von aliphatischen Kohlenwasserstoffen, die 1 bis 4 Kohlenstoff atome aufweisen, oder ihrer teilweise chlorierten Derivate

Info

Publication number: DE1468802C3
Authority: DE; Germany
Prior art keywords: oxygen; reaction; fluidized bed; oxychlorination; reactor
Prior art date: 1964-04-22
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

DE19651468802

Other languages

German (de)

English (en)

Other versions

DE1468802A1 (de

DE1468802B2 (de

Inventor

Lloyd Wilford Piester

Raymond Melvin Vancamp

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.)

PPG Industries Inc

Original Assignee

PPG Industries 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.)

1964-04-22

Filing date

1965-04-22

Publication date

1975-11-06

1965-04-22 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1969-04-10 Publication of DE1468802A1 publication Critical patent/DE1468802A1/de

1975-03-06 Publication of DE1468802B2 publication Critical patent/DE1468802B2/de

1975-11-06 Application granted granted Critical

1975-11-06 Publication of DE1468802C3 publication Critical patent/DE1468802C3/de

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 30
150000001338 aliphatic hydrocarbons Chemical class 0.000 title claims description 6
125000004432 carbon atom Chemical group C* 0.000 title claims description 3
238000006243 chemical reaction Methods 0.000 claims description 67
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 45
239000007789 gas Substances 0.000 claims description 43
239000003054 catalyst Substances 0.000 claims description 39
239000001301 oxygen Substances 0.000 claims description 36
229910052760 oxygen Inorganic materials 0.000 claims description 36
239000002245 particle Substances 0.000 claims description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 20
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 20
239000000460 chlorine Substances 0.000 claims description 16
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
239000012320 chlorinating reagent Substances 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 14
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
229930195733 hydrocarbon Natural products 0.000 description 11
239000000126 substance Substances 0.000 description 11
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
239000005977 Ethylene Substances 0.000 description 10
150000002430 hydrocarbons Chemical class 0.000 description 10
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
239000000463 material Substances 0.000 description 8
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
230000003197 catalytic effect Effects 0.000 description 7
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000001294 propane Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000009826 distribution Methods 0.000 description 4
239000001103 potassium chloride Substances 0.000 description 4
235000011164 potassium chloride Nutrition 0.000 description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000969 carrier Substances 0.000 description 3
-1 fuller's earth Chemical compound 0.000 description 3
229910001507 metal halide Inorganic materials 0.000 description 3
150000005309 metal halides Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000002485 combustion reaction Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000004880 explosion Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000004576 sand Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
229950011008 tetrachloroethylene Drugs 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
CZTQZXZIADLWOZ-UHFFFAOYSA-O 8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1SC2C(NC(=O)CC=3SC=CC=3)C(=O)N2C(C(=O)O)=C1C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-UHFFFAOYSA-O 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000530268 Lycaena heteronea Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910001514 alkali metal chloride Inorganic materials 0.000 description 1
229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000002826 coolant Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
238000013021 overheating Methods 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F28—HEAT EXCHANGE IN GENERAL
- F28D—HEAT-EXCHANGE APPARATUS, NOT PROVIDED FOR IN ANOTHER SUBCLASS, IN WHICH THE HEAT-EXCHANGE MEDIA DO NOT COME INTO DIRECT CONTACT
- F28D13/00—Heat-exchange apparatus using a fluidised bed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
- C07C17/152—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons
- C07C17/156—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons of unsaturated hydrocarbons
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F28—HEAT EXCHANGE IN GENERAL
- F28C—HEAT-EXCHANGE APPARATUS, NOT PROVIDED FOR IN ANOTHER SUBCLASS, IN WHICH THE HEAT-EXCHANGE MEDIA COME INTO DIRECT CONTACT WITHOUT CHEMICAL INTERACTION
- F28C3/00—Other direct-contact heat-exchange apparatus
- F28C3/10—Other direct-contact heat-exchange apparatus one heat-exchange medium at least being a fluent solid, e.g. a particulate material
- F28C3/12—Other direct-contact heat-exchange apparatus one heat-exchange medium at least being a fluent solid, e.g. a particulate material the heat-exchange medium being a particulate material and a gas, vapour, or liquid
- F28C3/16—Other direct-contact heat-exchange apparatus one heat-exchange medium at least being a fluent solid, e.g. a particulate material the heat-exchange medium being a particulate material and a gas, vapour, or liquid the particulate material forming a bed, e.g. fluidised, on vibratory sieves

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Mechanical Engineering (AREA)
General Engineering & Computer Science (AREA)
Physics & Mathematics (AREA)
Thermal Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DE19651468802 1964-04-22 1965-04-22 Verfahren zur Oxychlorierung von aliphatischen Kohlenwasserstoffen, die 1 bis 4 Kohlenstoff atome aufweisen, oder ihrer teilweise chlorierten Derivate Expired DE1468802C3 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US36169464A	1964-04-22	1964-04-22

Publications (3)

Publication Number	Publication Date
DE1468802A1 DE1468802A1 (de)	1969-04-10
DE1468802B2 DE1468802B2 (de)	1975-03-06
DE1468802C3 true DE1468802C3 (de)	1975-11-06

Family

ID=23423091

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19651468802 Expired DE1468802C3 (de)	1964-04-22	1965-04-22	Verfahren zur Oxychlorierung von aliphatischen Kohlenwasserstoffen, die 1 bis 4 Kohlenstoff atome aufweisen, oder ihrer teilweise chlorierten Derivate

Country Status (4)

Country	Link
CH (1)	CH448041A (fr)
DE (1)	DE1468802C3 (fr)
GB (1)	GB1049213A (fr)
NL (1)	NL6505142A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3987118A (en) *	1971-03-08	1976-10-19	Stauffer Chemical Company	Novel process for the oxychlorination of ethane

1965
- 1965-04-21 GB GB1689765A patent/GB1049213A/en not_active Expired
- 1965-04-22 CH CH559365A patent/CH448041A/fr unknown
- 1965-04-22 NL NL6505142A patent/NL6505142A/xx unknown
- 1965-04-22 DE DE19651468802 patent/DE1468802C3/de not_active Expired

Also Published As

Publication number	Publication date
NL6505142A (fr)	1965-10-25
DE1468802A1 (de)	1969-04-10
CH448041A (fr)	1967-12-15
GB1049213A (en)	1966-11-23
DE1468802B2 (de)	1975-03-06

Legal Events

Date	Code	Title
1975-11-06	C3	Grant after two publication steps (3rd publication)
1977-12-31	E77	Valid patent as to the heymanns-index 1977
1982-08-26	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE69206542T2 (de)	1996-05-15	Verfahren zur Herstellung von Ethylenoxyd.
DE2362738A1 (de)	1974-06-20	Verfahren zur herstellung von aethylendichlorid
DE10000584A1 (de)	2001-07-12	Verfahren zur katalytischen Gasphasenoxidation zu Maleinsäureanhydrid
DE1142349B (de)	1963-01-17	Verfahren zur Chlorierung von aliphatischen Kohlenwasserstoffen mit 1 bis 4 Kohlenstoffatomen
EP0031895B1 (fr)	1983-02-23	Procédé de préparation de 1,2-dichloroéthane
DE1468802C3 (de)	1975-11-06	Verfahren zur Oxychlorierung von aliphatischen Kohlenwasserstoffen, die 1 bis 4 Kohlenstoff atome aufweisen, oder ihrer teilweise chlorierten Derivate
DE1806036A1 (de)	1969-12-18	Verfahren zur katalytischen Umwandlung von AEthan in Vinylchlorid
DE1593250C3 (de)	1974-03-21	Verfahren zur Oxychlorierung von aliphatischen Kohlenwasserstoffen mit 1 bis 4 Kohlenstoffatomen oder ihrer teilweise chlorierten Derivate
DE3340624C1 (de)	1984-10-11	Verfahren zur Herstellung von 1,2-Dichlorethan aus Ethylen und Chlorgas
DE1074568B (de)	1960-02-04	Verfahren zur Herstellung von Vinylchlorid oder Vinylidenchlorid 5 4 5ö V St Amerika
DE1693042B2 (de)	1974-06-12	Verfahren zur Herstellung von Vinylchlorid
DE1668749A1 (de)	1971-09-02	Verfahren zur Herstellung von chlorierten Kohlenwasserstoffen
DE1952778C3 (de)	1981-01-08	Verfahren zum Entalkylieren von methylsubstituierten aromatischen Kohlenwasserstoffen
EP0001570B1 (fr)	1981-04-29	Procédé pour la préparation de formaldéhyde
DE1075592B (de)	1960-02-18	Verfahren zur Herstellung von Vinylchlorid oder Vinylidenchlorid
DE2714027A1 (de)	1977-10-13	Verfahren zur wiedergewinnung von chlorwasserstoff
DE2922375A1 (de)	1980-12-11	Verfahren zur herstellung von 1,2-dichlorethan
DD201582A5 (de)	1983-07-27	Verfahren zur herstellung von 1,2-dichlorethan
DE1279006B (de)	1968-10-03	Verfahren zur Oxychlorierung von aliphatischen Kohlenwasserstoffen
DE1468488C (de)	1973-02-15	Verfahren zur Oxychlorierung von ah phatischen Kohlenwasserstoffen, welche 1 bis 4 Kohlenstoffatome aufweisen
DE1593291C3 (de)	1973-12-06	Verfahren zur Herstellung von Trichlorethylen und Perchlorathylen
DE3935030A1 (de)	1991-04-25	Verfahren zur synthese von ethylenoxid
AT205471B (de)	1959-09-25	Verfahren zur Herstellung von Äthylenoxyd
DE2119237A1 (de)	1971-11-11	Verfahren zur Wiederaufladung der körnigen Massen einer Wanderschicht mit aktiven Elementen
DE2462171A1 (de)	1976-04-08	Verfahren zur reinigung von rohem phthalsaeureanhydrid