CA1110657A - Production de thiosemicarbazide - Google Patents

Production de thiosemicarbazide

Info

Publication number: CA1110657A
Authority: CA; Canada
Prior art keywords: thiocyanate; thiosemicarbazide; solution; hydrazinium; ammonia
Prior art date: 1978-05-09
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

CA323,716A

Other languages

English (en)

Inventor

Danny B. Barton

Chester W. Halbleib

Jack J. Lonsinger

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.)

Bayer Corp

Original Assignee

Mobay Corp

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.)

1978-05-09

Filing date

1979-03-19

Publication date

1981-10-13

1979-03-19 Application filed by Mobay Corp filed Critical Mobay Corp

1981-10-13 Application granted granted Critical

1981-10-13 Publication of CA1110657A publication Critical patent/CA1110657A/fr

Status Expired legal-status Critical Current

Links

BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 title claims abstract description 31
238000004519 manufacturing process Methods 0.000 title claims abstract description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 54
229910021529 ammonia Inorganic materials 0.000 claims abstract description 26
PVTHIYCCXJJALA-UHFFFAOYSA-N aminoazanium;thiocyanate Chemical compound [NH3+]N.[S-]C#N PVTHIYCCXJJALA-UHFFFAOYSA-N 0.000 claims abstract description 25
238000006317 isomerization reaction Methods 0.000 claims abstract description 25
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 22
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims abstract description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 10
230000000694 effects Effects 0.000 claims abstract description 6
238000010438 heat treatment Methods 0.000 claims abstract description 6
239000006227 byproduct Substances 0.000 claims abstract description 3
238000001816 cooling Methods 0.000 claims abstract description 3
238000005292 vacuum distillation Methods 0.000 claims abstract description 3
239000002904 solvent Substances 0.000 claims abstract 4
239000000243 solution Substances 0.000 claims description 33
238000000034 method Methods 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 12
238000004064 recycling Methods 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 2
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract description 10
239000012452 mother liquor Substances 0.000 abstract description 6
238000001914 filtration Methods 0.000 abstract description 4
150000001728 carbonyl compounds Chemical class 0.000 abstract description 2
238000002425 crystallisation Methods 0.000 abstract 1
230000008025 crystallization Effects 0.000 abstract 1
230000002035 prolonged effect Effects 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000003054 catalyst Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
239000002243 precursor Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000001577 simple distillation Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
DBLJAFVPFHRQSP-UHFFFAOYSA-N aminoazanium;sulfate Chemical compound NN.NN.OS(O)(=O)=O DBLJAFVPFHRQSP-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000000998 batch distillation Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
230000008016 vaporization Effects 0.000 description 1

Landscapes

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

CA323,716A 1978-05-09 1979-03-19 Production de thiosemicarbazide Expired CA1110657A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US90434578A	1978-05-09	1978-05-09
US904,345		1978-05-09

Publications (1)

Publication Number	Publication Date
CA1110657A true CA1110657A (fr)	1981-10-13

Family

ID=25418982

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA323,716A Expired CA1110657A (fr)	1978-05-09	1979-03-19	Production de thiosemicarbazide

Country Status (2)

Country	Link
CA (1)	CA1110657A (fr)
ZA (1)	ZA792210B (fr)

1979
- 1979-03-19 CA CA323,716A patent/CA1110657A/fr not_active Expired
- 1979-05-08 ZA ZA792210A patent/ZA792210B/xx unknown

Also Published As

Publication number	Publication date
ZA792210B (en)	1980-06-25

Legal Events

Date	Code	Title	Description
1998-10-13	MKEX	Expiry

Publication	Publication Date	Title
US4036888A (en)	1977-07-19	Process for the production of hydroxy-pivaldehyde
US3065231A (en)	1962-11-20	Production of triallyl isocyanurate
US2436311A (en)	1948-02-17	Preparation of n, n'ethyleneurea
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US3850924A (en)	1974-11-26	Process for preparing herbicidal triazines
US4256661A (en)	1981-03-17	Production of thiosemicarbazide
CA1110657A (fr)	1981-10-13	Production de thiosemicarbazide
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US2975177A (en)	1961-03-14	Intermediate product
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US2518264A (en)	1950-08-08	Method of preparing imidazolidones
CA1038886A (fr)	1978-09-19	Recuperation de carbonate de guanidium a partir de solutions aqueuses
US3948984A (en)	1976-04-06	Process of making penicillamine
US4082763A (en)	1978-04-04	Process for producing 3-hydrazino-4-amino-5-mercapto-1,2,4-triazole
CA2239545A1 (fr)	1997-06-05	Procede de preparation de cyclopentenones
JPH0239502B2 (ja)	1990-09-05	Monomechiruhidorajinnokaishuhoho
JPS6136270A (ja)	1986-02-20	２‐アルキル‐４，５‐ジヒドロキシメチルイミダゾールの製法