GB1374323A - Production of monohaloacyl halides - Google Patents

Production of monohaloacyl halides

Info

Publication number
GB1374323A
GB1374323A GB4505372A GB4505372A GB1374323A GB 1374323 A GB1374323 A GB 1374323A GB 4505372 A GB4505372 A GB 4505372A GB 4505372 A GB4505372 A GB 4505372A GB 1374323 A GB1374323 A GB 1374323A
Authority
GB
United Kingdom
Prior art keywords
carbonate
glycol
ketene
methyl
halides
Prior art date
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
GB4505372A
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.)
Monsanto Co
Original Assignee
Monsanto Co
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.)
Filing date
Publication date
Priority claimed from US00276280A external-priority patent/US3812183A/en
Application filed by Monsanto Co filed Critical Monsanto Co
Publication of GB1374323A publication Critical patent/GB1374323A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38—Acyl halides
    • C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
    • C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38—Acyl halides
    • C07C53/40—Acetyl halides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1374323 Monohaloacyl halides MONSANTO CO 29 Sept 1972 [26 Oct 1971 30 Sept 1971 (3) 31 July 1972 (3) 4 Aug 1972] 45053/72 Heading C2C Monohaloacyl halides are prepared by reacting an optionally substituted ketene with Cl 2 , Br 2 , I 2 or an interhalogen compound thereof in the presence of, as liquid solvent, one or more of (a) a cyclic carbonate of formula wherein R, R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> are each hydrogen, halogen, methyl, chloromethyl, phenyl or ethyl and n is 0 or 1; (b) an alkoxyalkyl ester of formula wherein R<SP>6</SP> and R<SP>8</SP> are each C 1-5 alkyl radicals and R<SP>7</SP> is C 1-5 alkylene, the total number of carbon atoms in R<SP>6</SP>, R<SP>7</SP> and B<SP>8</SP> being 3 to 10 inclusive; (c) an ester of formula wherein R<SP>9</SP> is alkyl of at least 2 carbon atoms (e.g. 2 to 7) and R<SP>10</SP> is C 1-4 alkyl; or (d) a glycol diester of formula wherein R<SP>20</SP> and R<SP>11</SP> are each C 1-4 alkyl, R<SP>12</SP> to R<SP>19</SP> are each hydrogen, methyl or ethyl, with not more than 3 of R<SP>12</SP> to R<SP>19</SP> being other than hydrogen and a and b are each 0 or 1. The ketene and halogen or interhalogen are preferably introduced concurrently into the solvent using a molar ratio of halogen (or interhalogen) to ketene of between 1 : 1 and 1À3 : 1. The required cyclic carbonate may be formed in situ from the corresponding unsaturated carbonate by addition of the halogenating agent. The process may be carried out continuously or batch-wise. Examples describe the halogenation of ketene, methyl ketene and phenyl ketene with Cl 2 and Br 2 to produce the corresponding monohaloacyl halides. Acyl halides and dihaloacyl halides are obtained as by-products. Exemplified and specified solvents are: ethylene carbonate, tetrachloroethylene carbonate, 1,2- and 1,3- butylene carbonates, chloromethylethylene carbonate, phenylethylene carbonate, 1,2- and 1,3-propylene carbonates, 2,2-dimethyl-1,3-propylene carbonate, 1,2-diethyl-1,3-propylene carbonate, 1,2-dimethylethylene carbonate, 1,2- diethylethylene carbonate, all the solvents falling into category (b), the methyl, ethyl, propyl and butyl esters of propionic, butyric, valeric, caproic, enanthylic and caprylic acids and the acetates, propionates, butyrates and valerates of ethylene glycol, propylene glycol, trimethylene glycol, tetramethylene glycol, 1,2- butylene glycol, 1,3-butylene glycol and isobutylene glycol. Comparative examples use as solvents: methyl, ethyl, butyl and hexyl acetates, carbon tetrachloride, 1,2-dichloroethylene, acetonitrile, benzonitrile and nitromethane.
GB4505372A 1971-09-30 1972-09-29 Production of monohaloacyl halides Expired GB1374323A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US18539671A 1971-09-30 1971-09-30
US18540271A 1971-09-30 1971-09-30
US18545071A 1971-09-30 1971-09-30
US19264771A 1971-10-26 1971-10-26
US27628172A 1972-07-31 1972-07-31
US27628272A 1972-07-31 1972-07-31
US00276280A US3812183A (en) 1971-09-30 1972-07-31 Preparation of monohaloacetyl halides
US27796172A 1972-08-04 1972-08-04

Publications (1)

Publication Number Publication Date
GB1374323A true GB1374323A (en) 1974-11-20

Family

ID=27575105

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4505372A Expired GB1374323A (en) 1971-09-30 1972-09-29 Production of monohaloacyl halides

Country Status (9)

Country Link
JP (1) JPS4840712A (en)
BE (1) BE789467A (en)
CA (1) CA985705A (en)
CH (1) CH576412A5 (en)
DK (1) DK153137C (en)
EG (1) EG11089A (en)
GB (1) GB1374323A (en)
IL (1) IL40466A (en)
IT (1) IT968446B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RO73277A (en) * 1973-07-16 1983-08-03 Monsanto Co,Us PROCEDURE FOR THE PREPARATION OF MONOHALOACIL HALOGENES
JPS5831768Y2 (en) * 1977-09-06 1983-07-14 ゼネラルパッカ−株式会社 Automatic collection device for unopened or unfilled packaging bags in packaging equipment
JPS5442280A (en) * 1977-09-09 1979-04-04 Tenchi Kikai Kk Device for separating each predetermined quantity of linked wrapped articles in seal wrapping machine
JPS5460086A (en) * 1977-10-20 1979-05-15 Kunio Tousaka Method of preventing erroneous cutting of small bag continuous band
WO1998050339A1 (en) * 1997-05-07 1998-11-12 Idemitsu Petrochemical Co., Ltd. 1-ACETOXY-3-n-PROPOXYPROPANE AND ETHER ALCOHOL SOLVENTS

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2862964A (en) * 1955-07-12 1958-12-02 Distillers Co Yeast Ltd Process for producing monochloro acetyl chloride

Also Published As

Publication number Publication date
EG11089A (en) 1976-12-31
IL40466A (en) 1976-04-30
CH576412A5 (en) 1976-06-15
IT968446B (en) 1974-03-20
BE789467A (en) 1973-03-29
IL40466A0 (en) 1972-11-28
JPS4840712A (en) 1973-06-15
DK153137C (en) 1988-12-19
DK153137B (en) 1988-06-20
CA985705A (en) 1976-03-16

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee